Acetic Acid → 2,3-Dihydroxy-4-ethoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene
Reaction equation
[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]=1Participants
6
Procedure
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:
Workup
- 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
Sources & evidence
- ORD record
- ord-d6e02c2cff4744f6aeb7b74f1b3b7359
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198302B2
Reaction notes
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