Acetic Acid → 2-Methylthio-5-(1-methoxycarbonylhexyl)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone

HRID 1197042Notes

Reaction equation

HRID 1197042 reaction equation
[CH3:1][S:2][C:3]1[C:4](=[O:35])[CH:5]([CH:24](O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]C(OC)=O)[CH:6]([CH:8]=[CH:9][CH:10]([O:16][Si](C(C)(C)C)(C)C)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1.[C:36]([OH:39])(=[O:38])C.O1CCC[CH2:41]1.O>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[C:4](=[O:35])[CH:5]([CH:24]([C:36]([O:39][CH3:41])=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:6]([CH:8]=[CH:9][CH:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 572430522-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

Product 1

HCID 571268992-Methylthio-5-(1-methoxycarbonylhexyl)-4-(3-hydroxy-1-octenyl)-2-cyclopentenoneYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 350 mg of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone obtained in Example 6 was added a solvent mixture of 10 ml of acetic acid, 5 ml of tetrahydrofuran, and 5 ml of water, and the mixture was stirred for 24 hours. Toluene was then added, and after concentration, the concentrate was diluted with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. Subsequently, the extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel chromatography to give 178 mg (yield 65%) of 2-methylthio-5-(1-methoxycarbonylhexyl)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone.

Workup

  1. concentrationafter concentration
  2. additionthe concentrate was diluted with saturated aqueous sodium hydrogencarbonate
  3. extractionextracted with ethyl acetate
  4. washSubsequently, the extract was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1171379d35ab4c269882b94c1226a591
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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