Acetic Acid → HCID 86745875, compound

HRID 1197060Notes

Reaction equation

HRID 1197060 reaction equation
[Si]([O:8][CH:9]([CH2:37][CH2:38][CH2:39][O:40][Si](C(C)(C)C)(C)C)/[CH:10]=[CH:11]/[CH:12]=[C:13]1[C:17](=[O:18])[C:16]([S:19][CH3:20])=[CH:15][C:14]1([CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[O:21][Si](C)(C)C)(C(C)(C)C)(C)C.C(O)(=O)C.O1CCCC1>O>[OH:8][CH:9]([CH2:37][CH2:38][CH2:39][OH:40])/[CH:10]=[CH:11]/[CH:12]=[C:13]1[C:17](=[O:18])[C:16]([S:19][CH3:20])=[CH:15][C:14]1([OH:21])[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 86745876HCID 86745876, compound

Product 1

HCID 86745875HCID 86745875, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 255 mg of 5-[(E)-4,7-bis(t-butyldimethylsilyloxy)-2-heptenylidene]-2-methylthio-4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 75 was added 20 ml of a mixture of acetic acid:tetrahydrofuran:water=3:1:1, and the mixture was stirred at room temperature for 26 hours. After concentration with an addition of toluene, saturated aqueous sodium hydrogencarbonate was added, and the mixture was extracted 3 times with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. After filtration and concentration, the concentrate was subjected to silica gel column chromatography to give 94 mg (yield 63%) of 5-[(E)-4,7-dihydroxy-2-heptenylidene]-4-hydroxy-2-methylthio-4-(4-phenoxybutyl)-2-cyclopentenone.

Workup

  1. concentrationAfter concentration
  2. additionwith an addition of toluene, saturated aqueous sodium hydrogencarbonate
  3. additionwas added
  4. extractionthe mixture was extracted 3 times with ethyl acetate
  5. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-017b8008e8a449fe9efc475db06ecc01
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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