Methanesulfonyl chloride → HCID 13754718, compound

HRID 986328Notes

Reaction equation

HRID 986328 reaction equation
[CH2:1]([C:5]1([O:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]([CH:10](O)[CH2:11][CH2:12][CH3:13])[C:8](=[O:15])[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].S(Cl)(C)(=O)=O.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1.C(OCC)(=O)C.CCCCCC.C1C=CC=CC=1.O>[CH2:1]([C:5]1([O:16][Si:17]([CH3:19])([CH3:20])[CH3:18])[CH:6]=[CH:7][C:8](=[O:15])/[C:9]/1=[CH:10]/[CH2:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13754716HCID 13754716, compound

Product 1

HCID 13754718HCID 13754718, compoundYield 49.4%

Reagents, catalysts & solvents 5

HCID 241BenzeneSolvent2×HCID 962WaterSolvent2×HCID 1049PyridineSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

40 mg (0.13 mmole) of 4-butyl-5-(1-hydroxybutyl)-4-trimethylsilyloxy-2-cyclopentenone was dissolved in 2 ml of pyridine, and at room temperature, 0.1 ml (1.3 mmoles) of mesyl chloride was added. The mixture was stirred for 8 hours. After the reaction, water was added, and the mixture was extracted with methylene chloride. The extract was dried, and concentrated, and 2 ml of benzene and 0.2 ml (1.3 mmoles) of DBU were added. The mixture was stirred at room temperature for 2 hours. Water was added, and the mixture was exracted with benzene. The extract was dried and concentrated, and the residue was chromatographed on a silica gel column (Merck silica gel 4 g, hexane:ethyl acetate=20:1) to give 18 mg (yield 48%) of 4-butyl-5-[(E)-butylidene]-4-trimethylsilyloxy-2-cyclopentenone (Rf=0.7, hexane:ethyl actate=3:1) and 5 mg (yield 14%) of its Z-isomer (Rf=0.75, hexane:ethyl acetate=3:1).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride
  3. customThe extract was dried
  4. concentrationconcentrated
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. customThe extract was dried
  7. concentrationconcentrated
  8. customthe residue was chromatographed on a silica gel column (Merck silica gel 4 g, hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-d325554559524be089d846898b10f893
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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