Water → HCID 67158875, compound

HRID 1891988Notes

Reaction equation

HRID 1891988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:24])[CH2:14][CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH:10]2[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:6][C:7]=1[Cl:8].C1CCN2C(=NCCC2)CC1.O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:24])[C:10]([C:20]([O:22][CH3:23])=[O:21])=[CH:11][CH2:12][CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86653594HCID 86653594, compound

Product 1

HCID 67158875HCID 67158875, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 2-(3,4-dichlorophenyl)-2-methyl-6-(methylsulfonyloxy)cyclohexanecarboxylate (185 mg) in benzene (5 mL) was stirred at rt and treated with DBU (131 μL). The mixture was heated to 60° C. and stirred for 36 h. The cooled mixture was treated with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under vacuum to provide methyl 6-(3,4-dichlorophenyl)-6-methylcyclohex-1-enecarboxylate (142 mg). Mass spectrum m/z 321.12 (M+Na+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-51c62a83e18d4860976fead2c088aac9
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

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