Dimethylformamide → 5-[[(1,1-Dimethylethyl)-diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid

HRID 399162ノート

反応式

HRID 399162 の反応式
[CH3:1][C:2]([Si:5]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[O:6][C:7]1[C:12]2[CH:13]([CH3:23])[CH:14]([CH2:19][CH2:20][CH2:21][OH:22])[C:15]([CH3:18])([CH3:17])[O:16][C:11]=2[CH:10]=[C:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=1)([CH3:4])[CH3:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:42].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.CN(C=O)C>O>[CH3:1][C:2]([Si:5]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[O:6][C:7]1[C:12]2[CH:13]([CH3:23])[CH:14]([CH2:19][CH2:20][C:21]([OH:42])=[O:22])[C:15]([CH3:17])([CH3:18])[O:16][C:11]=2[CH:10]=[C:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=1)([CH3:4])[CH3:3]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 2724130Cornforth reagentHCID 189701315-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol

生成物 1

HCID 189701375-[[(1,1-Dimethylethyl)-diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid収率 48.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2.2 g (3.97 mmol) of 5-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol and 7.47 g (19.86 mmol) of pyridinium dichromate (Aldrich) in anhy. DMF (Aldrich) was stirred at RT under argon for 20 hr. The reaction was diluted with water and extracted with EtOAc. The organic phase was dried and solvent removed under reduced pressure. The residue was then purified by repeated chromatography on silica gel to give 1.1 g (48%) of 5-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid as a pale yellow foam. HR EI MS: Calc M+, 572.3322; Observed, 572.3315. Ratio of 8:1 diastereoisomers as shown by 1H-NMR.

後処理

  1. extractionextracted with EtOAc
  2. customThe organic phase was dried
  3. customsolvent removed under reduced pressure
  4. customThe residue was then purified

出典と根拠

ORDレコード
ord-25011d0e8ae84d01aa6c6f6be9830a04
出典データセット
uspto-grants-1998_10
特許番号
US05817766

反応ノート

読み込み中…