Acetic Acid → HCID 56617818, compound

HRID 638632Notes

Reaction equation

HRID 638632 reaction equation
[CH2:1]([C@H:5]1[CH2:9]C[CH:7](C#N)[CH2:6]1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[C:17]([OH:20])(=[O:19])[CH3:18]>O.C(OCC)(=O)C>[CH2:1]([C@H:5]1[CH2:6][CH2:7][CH:18]([C:17]([OH:20])=[O:19])[CH2:9]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 56629887HCID 56629887, compound

Product 1

HCID 56617818HCID 56617818, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 73 mg of (1RS,3S)-3-butyl-1-cyanocyclopentane (prepared in Reference Example 13), 0.6 ml of conc. sulphuric acid, 0.6 ml of acetic acid and 0.6 ml of water was stirred for 1 hr. at 110° C. To the reaction solution, 30 ml of ethyl acetate and 20 ml of water were added. The oily layer which separated was washed with water, dried over anhydrous magnesium sulphate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 30 mg of the title compound having the following physical characteristics, in a 36.5% yield.

Workup

  1. customat 110° C
  2. customThe oily layer which separated
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-3af6bc94f9924e43bcc70708f9cec67c
Source dataset
uspto-grants-1985_12
Patent number
US04562207

Reaction notes

Loading…