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

HRID 516655

反応式

HRID 516655 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 157865963-Hydroxy-2,2-dimethyl-5-phenylpentanal収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b088dd1a3b264c0e82bd6badb58f889f
出典データセット
uspto-grants-2015_08
特許番号
US09114390B2

関連ノート

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