HRID399162

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

结构：[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-].c1cc[nH+]cc1.c1cc[nH+]cc1

HCID2724130

Chromic acid (H2Cr2O7), compd. with pyridine (1:2)

C10H12Cr2N2O7

结构：CCCCCc1cc2c(c(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)c1)C(C)C(CCCO)C(C)(C)O2

HCID18970131

未命名化合物

PRODUCTS

生成物

结构：CCCCCc1cc2c(c(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)c1)C(C)C(CCC(=O)O)C(C)(C)O2

HCID18970137

未命名化合物

收率 48.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

PROCEDURE

实验过程

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.

WORKUP

后处理

extractionextracted with EtOAc
customThe organic phase was dried
customsolvent removed under reduced pressure
customThe residue was then purified

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-25011d0e8ae84d01aa6c6f6be9830a04
来源数据集: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05817766
来源说明: uspto-grants-1998_10

反应 SMILES

[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]