Acetic Acid → HCID 56608063, compound

HRID 1197045Notes

Reaction equation

HRID 1197045 reaction equation
[CH3:1][S:2][C:3]1[C:4](=[O:34])[C:5](=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[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(O)(=O)C.O1CCCC1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[CH3:1][S:2][C:3]1[C:4](=[O:34])[C:5](=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:6]([CH:8]=[CH:9][CH:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 57070981HCID 57070981, compound

Product 1

HCID 56608063HCID 56608063, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

An amount of 1.42 g of 2-methylthio-5-(6-methoxycarbonylhexylidene-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone obtained in Example 22 was added to a mixture of acetic acid (2.1 ml), tetrahydrofuran (1.4 ml) and water (0.7 ml), and the mixture was stirred at room temperature for 2 days. To the reaction mixture saturated aqueous sodium hydrogencarbonate and ethyl acetate were added, and the product was extracted into the organic layer. The extract was washed with saturated aqueous sodium chloride, then dried over anhydrous magnesium sulfate and filtered, followed by concentration. The concentrate was subjected to silica gel chromatography to give 0.93 g (yield 85%) of 2-methylthio-5-(6-methoxycarbonylhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone.

Workup

  1. extractionthe product was extracted into the organic layer
  2. washThe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-ab34b6b281d94695a3c009380e31d8f4
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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