Bis(acetoxy)iodobenzene → 3-Hydroxy-2,2-dimethyl-5-phenylpentanal

HRID 516655

반응식

HRID 516655 반응식
C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)C.[CH3:16][C:17]([CH3:30])([CH:20]([OH:29])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][OH:19].O.C(=O)(O)[O-].[Na+]>ClCCl>[OH:29][CH:20]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]([CH3:16])([CH3:30])[CH:18]=[O:19]

참가 물질

5

반응물 3

HCID 21865429Bis(acetoxy)iodobenzeneHCID 855939482,2-Dimethyl-5-phenyl-1,3-pentanediolHCID 86585896Sodium bicarbonate water

생성물 1

HCID 157865963-Hydroxy-2,2-dimethyl-5-phenylpentanal수율 99%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

DMN-AZADO (2.00 mg, 0.012 mmol) and diacetoxyiodobenzene (117 mg, 0.362 mmol) were added to a dichloromethane solution (0.24 ml) of 2,2-dimethyl-5-phenylpentane-1,3-diol (50.2 mg, 0.241 mmol), and the mixture was stirred at room temperature for 15 min. This was followed by addition of saturated sodium bicarbonate water (1 ml) and a sodium thiosulfate solution (1 ml), and extraction with diethyl ether. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 3-hydroxy-2,2-dimethyl-5-phenylpentanal (49.2 mg, 92%).

후처리

  1. extractiona sodium thiosulfate solution (1 ml), and extraction with diethyl ether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b088dd1a3b264c0e82bd6badb58f889f
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09114390B2

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