Hydrochloric Acid → HCID 59442682, compound

HRID 657496Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.[O:15]=[C:16]1[CH2:21][CH2:20][C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:22]#[N:23])[CH2:18][CH2:17]1.Cl>C1COCC1>[OH:15][C:16]1([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=2)[CH2:21][CH2:20][C:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:22]#[N:23])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: -70 °C

Procedure

5.10 g of 4-bromothioanisole were dissolved in 50 ml of dry THF and 9.29 ml of an n-butyllithium solution (2.7 M in HEP) were added dropwise at a temperature between −65° C. and −70° C. The reaction mixture was stirred for 3 h at −70° C. Subsequently a solution of 5.00 g of 4-oxo-1-phenylcyclohexanecarbonitrile in 30 ml of THF was added dropwise at this temperature and the mixture was stirred for 10 min at −70° C. and 26 h at room temperature. The reaction mixture was then poured onto 400 g of ice, 100 ml of a 1 N hydrochloric acid were added and the mixture was extracted three times with 200 ml each of DCM. The combined extracts were dried over magnesium sulfate and the solvent was removed in vacuo. Chromatography of the residue on silica gel with EA/HEP (1:2) yielded 5.96 g of the title compound as a colorless oil.

Workup

stirringthe mixture was stirred for 10 min at −70° C. and 26 h at room temperature
additionwere added
extractionthe mixture was extracted three times with 200 ml each of DCM
dry with materialThe combined extracts were dried over magnesium sulfate
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-c22721975d46481a965b0e73484170d6
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076324B2

Reaction notes

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