Ethyl Acetate → HCID 57070981, compound

HRID 1587125Notes

Reaction equation

HRID 1587125 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:30]([O:32][CH3:33])=[O:31])[CH:6]([CH:8]=[CH:9][CH:10]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1.CN(C1C=CC=CN=1)C.CS(Cl)(=O)=O.C(OCC)(=O)C>ClCCl>[CH3:1][S:2][C:3]1[C:4](=[O:35])[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:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 572430522-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

Product 1

HCID 57070981HCID 57070981, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3.47 g of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone obtained in Example 6 in dichloromethane (30 ml) was added dimethylaminopyridine (1.54 g) and the mixture was cooled to 0° C. To the solution was dropwise added 0.59 ml of methanesulfonyl chloride, and the mixture was stirred at room temperature for 15 hours. To the reaction mixture were added ethyl acetate and an aqueous potassium hydrogensulfate, and the product was extracted into an organic layer. The extract was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate, and filtered, followed by concentration. The concentrate was subjected to silica gel chromatography to give 2.15 g (yield 64%) of 2-methylthio-5-(6-methoxycarbonylhexylidene)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone.

Workup

  1. extractionan aqueous potassium hydrogensulfate, and the product was extracted into an organic layer
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-d9f1866356454727a50c9e0533cb769d
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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