HCID 13362509, compound → HCID 131713664, compound

HRID 358368Notes

Reaction equation

HRID 358368 reaction equation
O1[CH:6]2[CH:2]1[C:3](=[O:15])[CH2:4][CH:5]2[O:7][Si:8]([C:11](C)(C)C)([CH3:10])C.[CH3:16][C:17]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][SH:26])[C:18]([O:20][CH3:21])=[O:19]>CO>[C:17]([CH:6]1[CH2:2][C:3](=[O:15])[C:4]([S:26][CH2:25][CH2:24][CH2:23][CH2:22][C:17]([C:18]([O:20][CH3:21])=[O:19])([CH3:27])[CH3:16])=[C:5]1[O:7][SiH:8]([CH3:10])[CH3:11])([CH3:22])([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 13362509HCID 13362509, compoundHCID 15681404Methyl 2,2-dimethyl-6-mercaptohexanoate

Product 1

HCID 131713664HCID 131713664, compoundYield 128.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.21 g (5.3 mmoles) of 2,3-epoxy-4(RS)-t-butyl-dimethylsilyloxycyclopentan-1-one was dissolved in 2.5 ml of methanol and then under cooling, 1.0 g (5.3 mmoles) of methyl 2,2-dimethyl-6-mercaptohexanoate was added. The mixture was stirred for 3 hours. After stirring, the solvent was removed by evaporation, and after adding water, the residue was extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The resulting crude product was chromatographed on a silica gel column using ethyl acetate-hexane (1/9) as an eluent to give 1.364 g (yield 64%) of 4(RS)-t-butyldi-methylsilyloxy-2-(5-methoxycarbonyl-5,5-dimethylpentylthio)-2-cyclopentenone.

Workup

  1. temperatureunder cooling
  2. stirringAfter stirring
  3. customthe solvent was removed by evaporation
  4. additionafter adding water
  5. extractionthe residue was extracted with ether
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe resulting crude product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-fa6ec93102a4461fbe67e9244dc4d190
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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