Lithium Hexamethyldisilazide → 4-[2-(2-Benzyloxyphenyl)-(E)-ethenyl]-2-hydroxybenzoic acid
반응식
C(OC1C=C(C)C=CC=1C(OC)=O)(=O)C.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1/[CH:30]=[CH:31]/[C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38]C)=[O:37])=[C:34]([OH:42])[CH:33]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OC1C=CC=CC=1/C=C\C1C=CC(C(OC)=O)=C(O)C=1)C1C=CC=CC=1.C(OC1C=CC=CC=1C=CC1C=CC(C(OC)=O)=CC=1F)C1C=CC=CC=1.FC1C=C(C=CC=1C)C(OC)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1/[CH:30]=[CH:31]/[C:32]1[CH:41]=[CH:40][C:35]([C:36]([OH:38])=[O:37])=[C:34]([OH:42])[CH:33]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1참가 물질
7
반응물 6
HCID 2733832Lithium Hexamethyldisilazide
HCID 18973756methyl 4-[2-(2-benzyloxyphenyl)-(E)-ethenyl]-2-hydroxybenzoate
HCID 18973767Methyl 3-fluoro-4-methylbenzoate
HCID 21841044Methyl 2-acetoxy-4-methylbenzoate
HCID 54449624Methyl 4-[2-(2-benzyloxyphenyl)ethenyl)-3-fluorobenzoate
HCID 70346139methyl 4-[2-(2-benzyloxyphenyl)-(Z)-ethenyl]-2-hydroxybenzoate생성물 1
실험 절차
Methyl 2-acetoxy-4-methylbenzoate was converted to a mixture of methyl 4-[2-(2-benzyloxyphenyl)-(E)-ethenyl]-2-hydroxybenzoate and methyl 4-[2-(2-benzyloxyphenyl)-(Z)-ethenyl]-2-hydroxybenzoate using the procedures described in Example 8 for the synthesis of methyl 4-[2-(2-benzyloxyphenyl)ethenyl)-3-fluorobenzoate from methyl 3-fluoro-4-methylbenzoate (using 2 equivalents of lithium hexamethyldisilazide in the final step). The isomers were separated by subjecting to chromatography on silica gel using a dichloromethane:hexane (1:2) as eluant. Further purification of the isomers was achieved by crystallisation.
후처리
- customThe isomers were separated
- customFurther purification of the isomers
- customwas achieved by crystallisation
출처 및 근거
- ORD 기록
- ord-d718f0b7e4234148bcc18cec5fc578ce
- 출처 데이터셋
- uspto-grants-1998_09
- 특허 번호
- US05811459
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