Methanol → 6-(Methoxycarbonylphenylthio)-6-tert.butyloxycarbonylhexanoic acid methyl ester

HRID 1588422Notes

Reaction equation

HRID 1588422 reaction equation
COC([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][C:13]2=[O:18])=[CH:7][CH:6]=1)=O.[CH3:26][OH:27]>C(OCC)(=O)C>[CH3:26][O:27][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]([S:11][C:8]1[CH:7]=[CH:6][CH:5]=[CH:10][C:9]=1[C:19]([O:21][CH3:22])=[O:20])[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20]

Participants

4

Reactant 2

HCID 887MethanolHCID 197556512-(4-Methoxycarbonylphenylthio)-2-tert.butoxycarbonylcyclohexanone

Product 1

HCID 572766676-(Methoxycarbonylphenylthio)-6-tert.butyloxycarbonylhexanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1 g (30.2 mmol) of 2-(4-methoxycarbonylphenylthio)2-tert.butoxycarbonylcyclohexanone is dissolved, together with 0.37 g (3.3 mmol) of potassium tert. butylate, in 100 ml of methanol of reagent purity and the solutions is left to stand for 2 hours at room temperature. It is then diluted with 500 ml of ethyl acetate and the organic phase is washed with water and a saturated sodium chloride solution, dried with sodium sulphate and concentrated by evaporation. After drying in a high vacuum 11.3 g of an oily product are obtained, which is sufficiently pure to be used for further reactions.

Workup

  1. waitthe solutions is left
  2. washthe organic phase is washed with water
  3. dry with materiala saturated sodium chloride solution, dried with sodium sulphate
  4. concentrationconcentrated by evaporation
  5. dry with materialAfter drying in a high vacuum 11.3 g of an oily product
  6. customare obtained

Sources & evidence

ORD record
ord-a6c827e290e24498b75fc06c989896f2
Source dataset
uspto-grants-1993_06
Patent number
US05221760

Reaction notes

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