反応 #6056

反応方程式

Sodium borohydride

2-Benzoyloxy-4-hydroxymethylcyclobutanone

borohydride

→

title compound

収率 101.8%

2-Benzoyloxy-4-hydroxymethylcyclobutanol

収率 101.8%

溶媒

acetic acid

—

glacial actetic acid

反応条件

後処理

1. 1
   その他The ice bath removed
2. 2
   workup.STIRRINGAfter stirring the reaction mixture for 35 minutes
3. 3
   その他the reaction was quenched with ~2 mL of methanol
4. 4
   濃縮the reaction mixture was concentrated in vacuo to a syrup
5. 5
   workup.DISSOLUTIONThe syrup was dissolved in 250 mL of ethyl acetate
6. 6
   洗浄the ethyl acetate solution was washed with water and 5% aqueous sodium bicarbonate
7. 7
   乾燥dried over magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated

実験手順

Glacial acetic acid in (25 mL) a 250 mL 3-neck flask was cooled in an ice bath under a stream of nitrogen. Sodium borohydride was added cautiously in portions over a 5 minute period. The ice bath removed and the reagent was used after stirring for 15 minutes at ambient temperature. 2-Benzoyloxy-4-hydroxymethylcyclobutanone (1.43 g, 6.5 mmol) from Step H was dissolved in 45 mL of glacial actetic acid and immediately treated with the above borohydride reagent. After stirring the reaction mixture for 35 minutes, the reaction was quenched with ~2 mL of methanol and the reaction mixture was concentrated in vacuo to a syrup. The syrup was dissolved in 250 mL of ethyl acetate and the ethyl acetate solution was washed with water and 5% aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to give 1.47 g of the title compound which was taken on to the next step without purification; MS DCI-NH3M/Z: 221 (M+H)+, 238 (M+NH4)+.

出典