Sodium borohydride → HCID 69527632、化合物

HRID 1828807ノート

反応式

HRID 1828807 の反応式
[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

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 22058586HCID 22058586、化合物

生成物 1

HCID 69527632HCID 69527632、化合物収率 94.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-27354e00d3b34f24ae97da49e0cbe085
出典データセット
uspto-grants-2006_06
特許番号
US07060721B1

反応ノート

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