Methanesulfonyl chloride → HCID 13784730, compound

HRID 986324Notes

Reaction equation

HRID 986324 reaction equation
[Cl:1][C:2]1[C:3](=[O:33])[CH:4]([CH:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:5]([CH2:12][CH2:13][CH:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])([O:7][Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:6]=1.CS(Cl)(=O)=O.N12CCCN=C1CCCCC2.S([O-])(O)(=O)=O.[K+]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3](=[O:33])/[C:4](=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])/[C:5]([CH2:12][CH2:13][CH:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])([O:7][Si:8]([CH3:10])([CH3:11])[CH3:9])[CH:6]=1.[Cl:1][C:2]1[C:3](=[O:33])/[C:4](=[CH:22]/[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])/[C:5]([CH2:12][CH2:13][CH:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])([O:7][Si:8]([CH3:10])([CH3:11])[CH3:9])[CH:6]=1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516920Potassium bisulfateHCID 20158384HCID 20158384, compound

Product 2

HCID 13784729HCID 13784729, compoundYield 30%HCID 13784730HCID 13784730, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

22 mg (44 micromoles) of 2-chloro-4-(3,7-dimethyloctyl)-5-(1-hydroxy-6-methoxycarbonyl)-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 4 was dissolved in 500 microliters of pyridine, and 50 microliters (646 micromoles) of methanesulfonyl chloride was added. The mixture was stirred for 1.5 hours. 200 microliters (1.34 mmoles) of 1,8-diazabicyclo[5.4.0]undec-7-ene was added, and the mixture was stirred for 30 minutes. A saturated aqueous solution of potassium hydrogen sulfate was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was chromatographed on a thin silica gel layer to give 6.3 mg (yield 30%) of 2-chloro-4-(3,7-dimethyloctyl)-5-[(Z)-6-methoxycarbonylhexylidene]-4-trimethylsilyloxy-2-cyclopentenone and 11.0 mg (yield 52%) of 2-chloro-4 -(3,7-dimethyloctyl)-5-[(E)-6-methoxycarbonylhexylidene]-4-trimethylsilyloxy-2-cyclopentenone.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed successively with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe residue was chromatographed on a thin silica gel layer

Sources & evidence

ORD record
ord-f171b99b13284b28aad164a64a019958
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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