Sodium borohydride → HCID 69527632, 화합물

HRID 1828807노트

반응식

HRID 1828807 반응식
[O:1]([CH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=1[Cl:28])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[O:1]([CH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][OH:25])=[CH:22][C:21]=1[Cl:28])[Si:2]([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 22058586HCID 22058586, 화합물

생성물 1

HCID 69527632HCID 69527632, 화합물수율 94.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 4-((tert-butyldiphenylsiloxy)methyl)-3-chlorobenzaldehyde (3.24 g) in ethanol (32 ml) was added sodium borohydride (149 mg) under ice-cooling and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated to about half amount. Water was added and the resulting product was extracted twice with diisopropyl ether. The organic layers were combined, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give 4-((tert-butyldiphenylsiloxy)methyl)-3-chlorobenzyl alcohol (3.08 g) as a colorless oil.

후처리

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated to about half amount
  3. additionWater was added
  4. extractionthe resulting product was extracted twice with diisopropyl ether
  5. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-27354e00d3b34f24ae97da49e0cbe085
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060721B1

반응 노트

불러오는 중…