Sodium hydride → HCID 19688588, compound

HRID 358372Notes

Reaction equation

HRID 358372 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[Si:16]([O:23][CH:24]1[CH2:28][C:27](=[O:29])[C:26]([S:30][CH2:31][CH2:32][CH2:33][CH:34]=O)=[CH:25]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C1C=CC=CC=1>[Si:16]([O:23][CH:24]1[CH2:28][C:27](=[O:29])[C:26]([S:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=[CH:25]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 20448834HCID 20448834, compound

Product 1

HCID 19688588HCID 19688588, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

96 mg (2.0 mmoles) of 50% sodium hydride was suspended in 5 ml of dry benzene, and 841 mg (4.0 mmoles) of methyl diethylphosphonoacetate was added. The mixture was stirred for 10 minutes. 600 mg (1.91 mmoles) of 4(RS)-t-butyldimethylsilyloxy-2-(4-oxobutylthio)-2-cyclopentenone was dissolved in 10 ml of dry benzene. The solution was stirred under ice cooling. To the resulting solution was added the above reaction mixture. The mixture was stirred further for 15 minutes. The reaction mixture was washed with a saturated aqueous solution of ammonium chloride, and extracted with ethyl acetate. The extract was dried over anhydrous dodium sulfate, and concentrated. The resulting oily product was chromatographed on a silica gel column using hexane/ethyl acetate (8/1) as an eluent to give 531 mg (yield 75%) of 4(RS)-t-butyldimethylsilyloxy-2-(5-methoxycarbonyl-trans-4-pentenylthio)-2-cyclopentenone.

Workup

  1. stirringThe solution was stirred under ice cooling
  2. additionTo the resulting solution was added the above reaction mixture
  3. stirringThe mixture was stirred further for 15 minutes
  4. washThe reaction mixture was washed with a saturated aqueous solution of ammonium chloride
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous dodium sulfate
  7. concentrationconcentrated
  8. customThe resulting oily product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-7a0ac63c6ffd49cbac9de268e524e4af
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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