Acetic Acid → 2,3-Dihydroxy-4-ethoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene
반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si](O[C:27]1[C:32](/[CH:33]=[CH:34]\[C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)=[CH:31]C=C(OCC)[C:28]=1[O:50][Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C.C(O)(=[O:60])C.O.[CH2:63]1[CH2:67][O:66][CH2:65][CH2:64]1>>[OH:50][C:28]1[C:64]([OH:60])=[C:65]([O:66][CH2:67][CH3:63])[CH:31]=[C:32](/[CH:33]=[CH:34]\[C:35]2[CH:36]=[C:37]([O:45][CH3:46])[C:38]([O:43][CH3:44])=[C:39]([O:41][CH3:42])[CH:40]=2)[CH:27]=1참가 물질
6
실험 절차
Tetrabutylammonium fluoride (0.75 mL, 0.75 mmol, 1M in THF) was added to a solution of 36 (0.21 g, 0.375 mmol) and glacial acetic acid (43 μL, 0.75 mmol) in THF 7 mL at 0° C. The reaction mixture was allowed to warm to room temperature overnight, then cooled to 0° C. and water was added. The reaction mixture was extracted with TBME (3×) and the organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was partitioned between CH3CN and cyclohexane and the CH3CN layer was separated and concentrated in vacuo to give the crude product. Purification by column chromatography (SiO2 1:1 EtOAc:cyclohexane) gave ZSB-81 (38 mg, 29%) as an 89:11 mixture of Z:E isomers:
후처리
- temperaturecooled to 0° C.
- extractionThe reaction mixture was extracted with TBME (3×)
- dry with materialthe organic phase was dried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe residue was partitioned between CH3CN and cyclohexane
- customthe CH3CN layer was separated
- concentrationconcentrated in vacuo
출처 및 근거
- ORD 기록
- ord-d6e02c2cff4744f6aeb7b74f1b3b7359
- 출처 데이터셋
- uspto-grants-2012_06
- 특허 번호
- US08198302B2
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