Sodium Bicarbonate → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 409485노트

반응식

HRID 409485 반응식
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:19].[Na+]>ClCCl>[CH3:1][O:8][C:9]([CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)=[O:19].[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

생성물 2

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl esterHCID 186672404-Benzyloxymethyl-cyclohexanecarbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of (4-benzyloxymethyl-cyclohexyl)-methanol (1.40 g, 6 mmol) in dichloromethane (28 mL) is added Dess-Marin reagent (2.53 g, 6 mmol) at 0° C., and the mixture is stirred for 0.5 hour while warming to room temperature. After addition of saturated aqueous NaHCO3, the aqueous layer is extracted with EtOAc. The combined organic layer (dried with MgSO4) is concentrated. The desired product, 4-benzyloxymethyl-cyclohexanecarbaldehyde, is obtained (1.07 g, 79%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

후처리

  1. extractionthe aqueous layer is extracted with EtOAc
  2. dry with materialThe combined organic layer (dried with MgSO4)
  3. concentrationis concentrated

출처 및 근거

ORD 기록
ord-2efa7ba89571432fac85bedb0f55173a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759365B2

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