1-(3,3-Dimethyl-1-p-tolyl-3H-inden-5-yl)-ethanone → 2-Trimethylsilanyl-ethyl 4-[3-(3,3-dimethyl-1-p-tolyl-3H-inden-5-yl)-3-oxo-propenyl]-3-fluoro-benzoate

HRID 2114089Notes

Reaction equation

HRID 2114089 reaction equation
[CH3:1][C:2]1([CH3:39])[C:11]2[CH:10]=[C:9]([C:12](=[O:31])[CH:13]=[CH:14][C:15]3[CH:29]=[CH:28][C:18]([C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])=[CH:17][C:16]=3[F:30])[CH:8]=[CH:7][C:6]=2[C:5]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)=[CH:4]C1.CC1(C)C2C(=CC=C(C(=O)C)C=2)C(C2C=CC(C)=CC=2)=C1>>[CH3:1][C:2]1([CH3:39])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](=[O:31])[CH:13]=[CH:14][C:15]3[CH:29]=[CH:28][C:18]([C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])=[CH:17][C:16]=3[F:30])[CH:10]=2)[C:5]([C:32]2[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=2)=[CH:4]1

Participants

3

Reactant 2

HCID 574238161-(3,3-Dimethyl-1-p-tolyl-3H-inden-5-yl)-ethanone2×HCID 688315342-Trimethylsilanyl-ethyl 4-[3-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-naphthalen-2-yl)-3-oxo-propenyl]-3-fluoro-benzoate2×

Product 1

HCID 688317082-Trimethylsilanyl-ethyl 4-[3-(3,3-dimethyl-1-p-tolyl-3H-inden-5-yl)-3-oxo-propenyl]-3-fluoro-benzoateYield 38%

Procedure

Following a procedure similar to that for the preparation of 2-trimethylsilanyl-ethyl 4-[3-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-naphthalen-2-yl)-3-oxo-propenyl]-3-fluoro-benzoate (Compound 8) while using 1-(3,3-dimethyl-1-p-tolyl-3H-inden-5-yl)-ethanone (Compound 14, 200 mg, 0.72 mmol) as the starting material yielded the title compound (145 mg, 38% yield) as a yellow solid:

Sources & evidence

ORD record
ord-03d6b2331253446196bc12c9de5c8230
Source dataset
uspto-grants-2008_10
Patent number
US07432388B2

Reaction notes

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