2-(4-Chlorophenyl)-4,4-dimethyl-1-cyclohexene-1-carboxaldehyde → HCID 67424937, compound

HRID 1520624Notes

Reaction equation

HRID 1520624 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[CH:16]=[O:17])=[CH:4][CH:3]=1.[CH3:18][Mg]Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][CH2:10][C:9]=2[CH:16]([OH:17])[CH3:18])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 872794142-(4-Chlorophenyl)-4,4-dimethyl-1-cyclohexene-1-carboxaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 67424937HCID 67424937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of EXAMPLE 218A (3.52 g) in tetrahydrofuran (30 ml) was slowly added methylmagnesium chloride (3 M in tetrahydrofuran, 7.08 ml) at −78° C. After the addition was completed, the reaction mixture was stirred at 0° C. for 30 minutes and ice-water was added. The resulting mixture was extracted with dichloromethane and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography, eluting with 0-100% dichloromethane in hexane to provide the title compound.

Workup

  1. customat −78° C
  2. additionAfter the addition
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 0-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-e2aa29f2c52f4bfb88c32cbc349b2fc0
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

Loading…