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

HRID 399162노트

반응식

HRID 399162 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-25011d0e8ae84d01aa6c6f6be9830a04
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817766

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