反応 #81124

反応方程式

3-((t-butyldimethylsilyloxy)methyl)-4-hydroxybut-2-eneoic acid

DIBAL

→

title product

2-((t-Butyldimethylsilyloxy)methyl)-but-2-ene-1,4-diol

溶媒

methylene chloride

反応条件

後処理

1. 1
   温度cooled in a dry ice bath
2. 2
   温度to warm to room temperature
3. 3
   workup.STIRRINGstirred for 16 hours
4. 4
   温度The mixture was cooled to -78° C.
5. 5
   その他quenched with 1.53 mL of methanol and 2.55 mL of water
6. 6
   ろ過The mixture was filtered
7. 7
   濃縮the filtrate concentrated
8. 8
   その他chromatographed on silica gel
9. 9
   洗浄eluting with 50% and 90% ethyl acetate in hexane
10. 10
    その他The solvent was removed
11. 11
    その他the product dried

実験手順

A 2.210 g (9.69 mmol) sample of 3-((t-butyldimethylsilyloxy)methyl)-4-hydroxybut-2-eneoic acid, 1,4-lactone, from Example 336A, was dissolved in 6 mL of methylene chloride, cooled in a dry ice bath, and 14.2 mL (21.3 mmol) of DIBAL was added. The mixture was stirred at 78° C. for 4 hours, allowed to warm to room temperature and stirred for 16 hours. The mixture was cooled to -78° C. and quenched with 1.53 mL of methanol and 2.55 mL of water. The mixture was filtered, and the filtrate concentrated and chromatographed on silica gel, eluting with 50% and 90% ethyl acetate in hexane. The solvent was removed and the product dried to afford 1.055 g of the title product, which was taken directly to the next step.

出典