Triphenylphosphine → methyl (R)-7-(4-fluorophenyl)-7-(5-hydroxy-6,7-dimethylindan-4-yl)heptanoate

HRID 1707812Notes

Reaction equation

HRID 1707812 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[CH2:7][CH2:6][CH2:5]2.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20](O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC([N+](C(OCC)=O)=[N-])=O)C>ClCCCl>[OH:1][C:2]1[C:3]([C@@H:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[C:4]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 10562892methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoateHCID 111265795-Hydroxy-6,7-dimethylindanHCID 14357405Diethyldiazodicarboxylate

Product 1

HCID 10692267methyl (R)-7-(4-fluorophenyl)-7-(5-hydroxy-6,7-dimethylindan-4-yl)heptanoateYield 37.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 5-hydroxy-6,7-dimethylindan (0.96 g, 5.9 mmol), methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate (0.30 g, 1.2 mmol) and triphenylphosphine (0.46 g, 1.8 mmol) in 1,2-dichloroethane (15 ml) was added dropwise a solution of 95% diethyldiazodicarboxylate (DEAD) (0.33 ml) in 1,2-dichloroethane (3 ml) at 10° C. taking 30 minutes. The mixture was stirred for one hour at the same temperature range, then the solvent was distilled off under reduced pressure. The residue was subjected to a silica gel coluann chromatography to give 0.18 g of methyl (R)-7-(5-hydroxy-6,7-dimethylindan-4-yl)-7-(4-fluorophenyl)heptanoate. Likewise, Compound 1, 5-8 and 10-17 were prepared.

Workup

  1. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-df37594f0a0e43b6b01ebebc460a4cd0
Source dataset
uspto-grants-1994_10
Patent number
US05354913

Reaction notes

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