反応 #1049542

反応方程式

1.2-O-Dihexadecyl-3-methylthio-1.2-propanediol Racemic 1,2-O-dihexadecyl-3-bromo-1,2-propanediol

1,2-O-dihexadecyl-3-bromo-1,2-propanediol

sodium thiomethoxide

sodium thiomethoxide

ethyl acetate

tetrahydrofuran

→

1,2-O-dihexadecyl-3-methylthio-1,2-propanediol

収率 90.0%

溶媒

hexane

chloroform

反応条件

後処理

1. 1
   その他equipped with a magnetic stir bar
2. 2
   workup.WAITAfter an additional 3 hr
3. 3
   ろ過the mixture was filtered
4. 4
   洗浄the filtrate was washed with 50 ml tetrahydrofuran
5. 5
   濃縮The combined filtrates were concentrated under vacuum
6. 6
   その他a rotary evaporator
7. 7
   その他to afford a yellow residue
8. 8
   洗浄the organic solution was washed twice with 25 ml of a concentrated solution of sodium bicarbonate
9. 9
   乾燥The organic phase was then dried over anhydrous magnesium sulfate
10. 10
    濃縮concentrated on a rotary evaporator under vacuum
11. 11
    その他to afford the crude product as a pale yellow oily residue
12. 12
    その他The crude product was purified by column chromatography on a silica gel 60 (E. Merck, Germany) column
13. 13
    その他The fractions collected
14. 14
    workup.ADDITIONThose fractions containing pure product
15. 15
    濃縮concentrated

実験手順

Synthesis of 1.2-O-Dihexadecyl-3-methylthio-1.2-propanediol Racemic 1,2-O-dihexadecyl-3-bromo-1,2-propanediol (from Step 1), 2.0 g (3.3 mmoles), was dissolved into 100 ml of dry tetrahydrofuran in a 250 ml round bottom flask equipped with a magnetic stir bar. To this solution was added 2.33 g (33.2 mmoles) of sodium thiomethoxide powder and the reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC (silica gel, 5% ethyl acetate in hexane) and an additional 490 mg (7 mmoles) of sodium thiomethoxide was added to the reaction. After an additional 3 hr, the mixture was filtered and the filtrate was washed with 50 ml tetrahydrofuran. The combined filtrates were concentrated under vacuum using a rotary evaporator to afford a yellow residue. This residue was dissolved into 50 ml chloroform and the organic solution was washed twice with 25 ml of a concentrated solution of sodium bicarbonate. The organic phase was then dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator under vacuum to afford the crude product as a pale yellow oily residue. The crude product was purified by column chromatography on a silica gel 60 (E. Merck, Germany) column using a step gradient of 0 to 10% ethyl acetate in hexane. The fractions collected were screened by TLC. Those fractions containing pure product were pooled and concentrated to afford 1,2-O-dihexadecyl-3-methylthio-1,2-propanediol in 90% yield.

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