methyl (R)-7-(4-fluorophenyl)-7-(5-hydroxy-6,7-dimethylindan-4-yl)heptanoate → methyl (R)-7-(4-fluorophenyl)-7-(5-hydroxy-6,7-dimethyl-l-oxoindan-4-yl)heptanoate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]2[C:26]([OH:27])=[C:25]([CH3:28])[C:24]([CH3:29])=[C:23]3[C:19]=2[CH2:20][CH2:21][CH2:22]3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=[O:31].[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]2[C:26]([OH:27])=[C:25]([CH3:28])[C:24]([CH3:29])=[C:23]3[C:19]=2[CH2:20][CH2:21][C:22]3=[O:31])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl (R)-7-(4-fluorophenyl)-7-(5-hydroxy-6,7-dimethylindan-4-yl)heptanoate (16.0 g, 40.2 mmol) in toluene (640 ml) was added a mixture of pyridinium chlorochromate (43.3 g, 0.20 ml) and Celite (52 g) at 0° C. under argon atmosphere, followed by stirring for 23 hours at the same temperature. Insolubles were filtered and washed with toluene. The filtrate and washes were combined and concentrated. The residue was subjected to a silica gel column chromatography to give methyl (R)-7-(4-fluorophenyl)-7-(5-hydroxy-6,7-dimethyl-l-oxoindan-4-yl)heptanoate (10.9 g). The compound obtained is the same as Compound No. 15. Likewise, Compound 29 was prepared. Physico-chemical properties and spectral data are shown in [Table 6].
Workup
- filtrationInsolubles were filtered
- washwashed with toluene
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-05e3b1ced02d431f96740e05179da436
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420363
Reaction notes
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