4-Bromoanisole → HCID 21196480, compound

HRID 1067141Notes

Reaction equation

HRID 1067141 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]1([C:16]2[N:17]=[C:18]([CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]3=[O:34])[O:19][C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1.CCCCCC.C([Li])CCC>[C:10]1([C:16]2[N:17]=[C:18]([CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]3([C:7]3[CH:2]=[CH:3][CH:4]=[C:5]([O:8][CH3:9])[CH:6]=3)[OH:34])[O:19][C:20]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 77304-BromoanisoleHCID 131268312-[(4,5-Diphenyl-1,3-oxazol-2-yl)methyl]cyclohexan-1-one

Product 1

HCID 21196480HCID 21196480, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418244HCID 178418244, compoundSolvent

Procedure

To a solution of 4-bromoanisole (1.00 g) in tetrahydrofuran (4 ml), n-butyllithium hexane solution (1.56M, 3.4 ml) was added at −78° C. under a flow of nitrogen. After stirring for 0.5 hour, a solution of 2-[(4,5-diphenyloxazol-2-yl)methyl]cyclohexan-1-one (1.36 g) in tetrahydrofuran (3 ml) was added below −50° C. to the reaction mixture and stirred for 0.5 hour. After usual workup, the crude product was purified by column chromatography (silica gel 50 g, eluent; hexane/ethyl acetate=9 then 4) to give 2-[(4,5-diphenyloxazol-2-yl)methyl]-1-(3-methoxyphenyl)-1-cyclohexanol (1.01 g) as a foam.

Workup

  1. stirringstirred for 0.5 hour
  2. customAfter usual workup, the crude product was purified by column chromatography (silica gel 50 g, eluent

Sources & evidence

ORD record
ord-6e418e080592481aacff241b77ef5010
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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