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

HRID 2168372Notes

Reaction equation

HRID 2168372 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-ffd92c526d3449f28eb4189c320c107c
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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