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]-benzoate

HRID 853199Notes

Reaction equation

HRID 853199 reaction equation
CC1(C)C2[CH:10]=[C:9]([C:12](=[O:30])[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][CH:16]=3)[CH:8]=[CH:7]C=2C(C2C=CC(C)=CC=2)=CC1.[CH3:39][C:40]1([CH3:59])[C:48]2[C:43](=CC=C(C(=O)C)C=2)[C:42]([C:52]2[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=2)=[CH:41]1>>[CH3:39][C:40]1([CH3:59])[C:48]2[C:43](=[CH:7][CH:8]=[C:9]([C:12](=[O:30])[CH:13]=[CH:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:26])[CH3:27])=[O:20])=[CH:28][CH:29]=3)[CH:10]=2)[C:42]([C:52]2[CH:53]=[CH:54][C:55]([CH3:58])=[CH:56][CH:57]=2)=[CH:41]1

Participants

3

Reactant 2

HCID 574238161-(3,3-Dimethyl-1-p-tolyl-3H-inden-5-yl)-ethanone2×HCID 688321412-Trimethylsilanyl-ethyl 4-[3-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-naphthalen-2-yl)-3-oxo-propenyl]-benzoate2×

Product 1

HCID 688291732-Trimethylsilanyl-ethyl 4-[3-(3,3-dimethyl-1-p-tolyl-3H-inden-5-yl)-3-oxo-propenyl]-benzoateYield 25%

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]-benzoate (Compound 6) 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 (93 mg, 25% yield) as a yellow solid:

Sources & evidence

ORD record
ord-776a443f85904966ae6048ded2c95e65
Source dataset
uspto-grants-2007_08
Patent number
US07253319B2

Reaction notes

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