tert-Butyldimethylsilyl chloride → HCID 20448820, compound

HRID 358369Notes

Reaction equation

HRID 358369 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH3:14])=[CH:3]1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)P(=O)(N(C)C)N(C)C>[Si:19]([O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH3:14])=[CH:3]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 20448837HCID 20448837, compound

Product 1

HCID 20448820HCID 20448820, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

726 mg of 4(RS)-hydroxy-2-(5-methoxycarbonyl-5-methylpentylthio)-2-cyclopentenone and 596 mg (3.96 mmoles) of t-butyldimethylsilyl chloride were dissolved in 10 ml of hexamethylphosphoric triamide, and the reaction was performed at 0° C. for 20 hours. After the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried and concentrated to give 2.09 g of a crude product. The crude product was chromatographed on a silica gel column using hexane/ethyl acetate (4/1) as an eluent to give 594 mg (1.54 mmoles; yield 58.3%) of 4(RS)-t-butyldimethylsilyloxy-2-(5-methoxycarbonyl-5-methyl-pentylthio)-2-cyclopentenone.

Workup

  1. customAfter the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated
  5. customto give 2.09 g of a crude product
  6. customThe crude product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-50583f0b81c940adb1260bac362b6284
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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