Sodium borohydride → 4-Hydroxymethyl-2-triethylsilylfuran

HRID 1090879

반응식

HRID 1090879 반응식
[BH4-].[Na+].[CH2:3]([Si:5]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]1[O:7][CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[CH3:4]>CO>[OH:12][CH2:11][C:9]1[CH:10]=[C:6]([Si:5]([CH2:13][CH3:14])([CH2:15][CH3:16])[CH2:3][CH3:4])[O:7][CH:8]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

생성물 1

HCID 150370354-Hydroxymethyl-2-triethylsilylfuran

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Sodium borohydride (353 mg, 0.93 mmol) was added portion-wise to a solution of 2-triethylsilyl-4-furaldehyde (1.64 g, 7.79 mmol) in methanol (10 ml) at 0°. After 1 hour, most of the methanol was evaporated and the residue dissolved in a minimum amount of dilute hydrochloric acid. Extraction (ethyl acetate), drying (magnesium sulfate) and evaporation gave an oil, which was purified by flash chromatography on silica using 20% ethyl ether/hexane. Fractions with Rf of about 0.07 (10% ethyl ether/hexane) gave after evaporation the title alcohol as a colorless oil.

후처리

  1. custommost of the methanol was evaporated
  2. dissolutionthe residue dissolved in a minimum amount of dilute hydrochloric acid
  3. extractionExtraction (ethyl acetate)
  4. customdrying
  5. custom(magnesium sulfate) and evaporation
  6. customgave an oil, which
  7. customwas purified by flash chromatography on silica using 20% ethyl ether/hexane
  8. customFractions with Rf of about 0.07 (10% ethyl ether/hexane) gave
  9. customafter evaporation the title alcohol as a colorless oil

출처 및 근거

ORD 기록
ord-9179d560cfaf44ebafba3cd476961c5e
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082954

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