Borohydride → 2-Benzoyloxy-4-hydroxymethylcyclobutanol

HRID 5960

반응식

HRID 5960 반응식
[BH4-].[Na+].[C:3]([O:11][CH:12]1[CH2:15][CH:14]([CH2:16][OH:17])[C:13]1=[O:18])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BH4-]>C(O)(=O)C>[C:3]([O:11][CH:12]1[CH2:15][CH:14]([CH2:16][OH:17])[CH:13]1[OH:18])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 197943182-Benzoyloxy-4-hydroxymethylcyclobutanone

생성물 1

HCID 197942892-Benzoyloxy-4-hydroxymethylcyclobutanol수율 101.8%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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)+.

후처리

  1. customThe ice bath removed
  2. stirringAfter stirring the reaction mixture for 35 minutes
  3. customthe reaction was quenched with ~2 mL of methanol
  4. concentrationthe reaction mixture was concentrated in vacuo to a syrup
  5. dissolutionThe syrup was dissolved in 250 mL of ethyl acetate
  6. washthe ethyl acetate solution was washed with water and 5% aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c6befcbde27c4bafadace118dde28422
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246931

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