Boron Trichloride → Ethyl (2E)-3-{2-[4-(hydroxy)phenyl]-1-cyclohexyl-1H-imidazol-4-yl}-2-methyl-2-propenoate

HRID 2216535Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:17]=[C:18](/[CH:20]=[C:21](\[CH3:27])/[C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:17]=[C:18](/[CH:20]=[C:21](\[CH3:27])/[C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=2)=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 11293723Ethyl (2e)-3-{2-[4-(benzyloxy)phenyl]-1-cyclohexyl-1h-imidazol-4-yl}-2-methyl-2-propenoate

Product 1

HCID 136008555Ethyl (2E)-3-{2-[4-(hydroxy)phenyl]-1-cyclohexyl-1H-imidazol-4-yl}-2-methyl-2-propenoateYield 60%

Procedure

According to the procedure for preparation of 4.3, ester 13.1 (167 mg, 0.376 mmol) was treated with BCl3 (1.88 mmol) to yield 80 mg (60%) of 13.3. MS (ESI) 355.3 (MH+).

Sources & evidence

ORD record: ord-c511b1ee168d4cbcaba853f69bcf3b0e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112601B2

Reaction notes

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