Water → HCID 68567759, compound

HRID 1584125Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2C2(O)CCCCC2)=[CH:5][CH:4]=1.BrC1C=CC=CC=1C1SC=C(C)C=1.C([Li])CCC.C1(=[O:46])CCCCC1.[OH2:47]>O1CCCC1.C(OCC)(=O)C>[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1.[CH3:1][S:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)(=[O:46])=[O:47]

Participants

Conditions

Temperature: -78 °C

Procedure

2-(4'-methylthiophenyl)-1-(1-hydroxy-1-cyclohexyl)-benzene: 2-Bromo-(4'-methylthiophenyl) benzene (3.02 g, 10.8 mmol) was dissolved in tetrahydrofuran (35 ml), cooled to -78° C. and n-butyllithium (4.5 ml, 11.3 mmol) was slowly added. The pale yellow mixture was stirred at -78° C. for 2 h followed by addition of cyclohexanone (1.3 ml, 12.9 mmol). The reaction was stirred for 18 h and allowed to warm to room temperature. The reaction was diluted with water and ethyl acetate. The aqueous layer was extacted with ethyl acetate and the combined organic layers were dried, filtered and concentrated. Purification by chromatography on silica gel using 6:1 hexane/ethyl acetate as eluant afforded the desired product (2.51 g., 77%) as a clear oil; 1H NMR (CDCl3) d 7.58 (d, 1H), 7.36 (m, 2H), 7.27 (m, 4H), 7.04 (dd, 1H), 2.53 (s, 3H), 2.34 (t, 1H), 1.83-1.10 (m, 10H), Mass spectrum (high resolution, EI/DEP) calc'd M+ 298.139137; found M+ 298.138665.

Workup

stirringThe reaction was stirred for 18 h
temperatureto warm to room temperature
customthe combined organic layers were dried
filtrationfiltered
concentrationconcentrated
customPurification by chromatography on silica gel using 6:1 hexane/ethyl acetate as eluant

Sources & evidence

ORD record: ord-b8a5083caca14927bfb23f84133beb68
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932586

Reaction notes

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