Water → HCID 178418381, compound

HRID 1659

Reaction equation

HRID 1659 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26].O>CN(C)C=O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 178418412HCID 178418412, compound

Product 1

HCID 178418381HCID 178418381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1 g (3.75 mmol) of trans-O-acetyl-4-(4-chloromethylphenyl)-cyclohexanol in 10 ml of dimethylformamide is mixed with 0.52 g (3.75 mmol) of potassium carbonate and 0.27 g (3.75 mmol) of diethylamine. This mixture is heated to 50° C. for 6 hours with stirring, then water is added and the mixture is extracted with methylene chloride. The organic phase is dried, evaporated down in vacuo and the residue remaining is purified by column chromatography (aluminium oxide basic, activity stage III, ICN; petroleum ether/ethyl acetate=15:1). Colourless oil.

Workup

  1. extractionthe mixture is extracted with methylene chloride
  2. customThe organic phase is dried
  3. customevaporated down in vacuo
  4. customthe residue remaining is purified by column chromatography (aluminium oxide basic, activity stage III, ICN; petroleum ether/ethyl acetate=15:1)

Sources & evidence

ORD record
ord-d5a8195f23794884af3a23a8c8f6148d
Source dataset
uspto-grants-1998_03
Patent number
US05726205

Linked notes

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