Acetic Acid → 2-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

HRID 1587123Notes

Reaction equation

HRID 1587123 reaction equation
[CH3:1][S-:2].[Na+].C(O)(=O)C.C(N(CC)CC)C.O1[CH:20]2[CH:16]1[C:17](=[O:48])[CH:18]([CH:37]([OH:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:19]2[CH:21]=[CH:22][CH:23]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CO.O>[CH3:1][S:2][C:16]1[C:17](=[O:48])[CH:18]([CH:37]([OH:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:19]([CH:21]=[CH:22][CH:23]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:20]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 4378561Sodium methanethiolateHCID 54508019HCID 54508019, compound

Product 1

HCID 572430522-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenoneYield 100.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium thiomethoxide (2.30 g) in methanol (100 ml) was cooled to 0° C., acetic acid (2.82 ml) was added, the mixture was stirred for 5 minutes, Triethylamine (915 ml) was added, and a solution of 2,3-epoxy-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)cyclopentanone (3.26 g) in methanol (40 ml) was added. After stirring at room temperature for 12 hours, water was added to the mixture, and the mixture extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered, followed by concentration. The concentrate was subjected to silica gel chromatography to give 3.47 g (yield 96%) of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone.

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-7c0efcb98aa24d539268dfb6ef3998c4
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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