Acetic Acid → 1,2-Dihydroxy-3-allyloxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

HRID 218268Notes

Reaction equation

HRID 218268 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][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][CH:30]=[C:29]([O:47][CH2:48][CH:49]=[CH2:50])[C:28]=1[O:51][Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C.C(O)(=O)C.O>C1COCC1>[OH:26][C:27]1[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:31][CH:30]=[C:29]([O:47][CH2:48][CH:49]=[CH2:50])[C:28]=1[OH:51]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 601306841,2-di(t-butyldimethylsilyloxy)-3-allyloxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

Product 1

HCID 601306781,2-Dihydroxy-3-allyloxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (0.24 mL, 0.24 mmol, 1M in THF) was added to a solution of 1,2-di(t-butyldimethylsilyloxy)-3-allyloxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene (69 mg, 0.120 mmol) and glacial acetic acid (14 μL, 0.24 mmol) in THF 4 mL at 0° C. The reaction mixture was allowed to warm to rt overnight, then cooled to 0° C. and water was added. The reaction mixture was extracted with t-BuOMe (3×) and the organic phase was dried (Na2SO4) and evaporated to dryness. Purification by column chromatography (SiO2 3:7 EtOAc:cyclohexane) gave ZSB-84 (36 mg, 84%) as an 96:4 mixture of Z:E isomers:

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe reaction mixture was extracted with t-BuOMe (3×)
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. customevaporated to dryness
  5. customPurification by column chromatography (SiO2 3:7 EtOAc:cyclohexane)
  6. customgave ZSB-84 (36 mg, 84%)
  7. additionas an 96:4 mixture of Z

Sources & evidence

ORD record
ord-65ee6737982c4a37b1ce3fd32773914e
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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