Thionyl Chloride → 4'-(4-Fluoro-6-methyl-3-trifluoromethyl-1H-inden-2-yl)4-propylbicyclohexyl

HRID 1244191Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH3:27])[CH:5]=[C:6]2[C:10]=1[C:9](=O)[CH:8]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19]3)[CH2:14][CH2:13]1)[CH2:7]2.[F:28][C:29]([Si](C)(C)C)([F:31])[F:30].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F-].[K+].S(Cl)(Cl)=O>O1CCCC1.CO.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH3:27])[CH:5]=[C:6]2[C:10]=1[C:9]([C:29]([F:31])([F:30])[F:28])=[C:8]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19]3)[CH2:14][CH2:13]1)[CH2:7]2

Participants

Conditions

Temperature: 0 °C

Procedure

8.5 g (0.023 mol) of 7-fluoro-5-methyl-2-(4′-propylbicyclohexyl-4-yl)-indan-1-one are dissolved in 50 ml of-tetrahydrofuran and the solution is cooled down to 0° C. 3.7 ml (0.025 mol) of trifluoromethyltrimethylsilane are added. 0.1 ml of tetrabutylammonium fluoride (1 M solution in THF) are added. After the reaction has ended, the mixture is subjected to conventional workup, and then the product is taken up in 40 ml of methanol, 200 mg of potassium fluoride are added and the mixture is refluxed for 10 hours. The resulting carbinol is dissolved in 30 ml of pyridine and 1.7 ml (0.024 mol) of thionyl chloride are added dropwise. The mixture is stirred for 10 hours at room temperature and then subjected to conventional workup.

Workup

temperaturethe mixture is refluxed for 10 hours

Sources & evidence

ORD record: ord-0939614006f744c5abe2b68dd2e3198d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122228B2

Reaction notes

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