2-(3-Chlorophenyl)-2-methylpropanal → 3-(3-Chlorophenyl)-3-methylbutan-2-ol

HRID 83867Notes

Reaction equation

HRID 83867 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]([OH:10])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 820751242-(3-Chlorophenyl)-2-methylpropanalHCID 178418689HCID 178418689, compound

Product 1

HCID 667407143-(3-Chlorophenyl)-3-methylbutan-2-olYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(3-chlorophenyl)-2-methylpropanal (4.6 g, 25.7 mmol) in THF (150 mL) at 0° C. was added MeMgBr (3M in ether, 17.1 mL, 51.3 mmol, 2 eq) dropwise over 2 h. After stirring 1 h at 0° C., the reaction was allowed to warm to room temperature, quenched with 1N HCl and then extracted with EtOAc. The extracts were dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1) to give 3-(3-chlorophenyl)-3-methylbutan-2-ol (3.9 g, 78%). 1H NMR (400 MHz, CDCl3) δ 7.36 (s, 1H), 7.28 (m, 2H), 7.18 (m, 1H), 3.85 (q, 1H), 1.32 (d, J=6.4 Hz, 6H), 1.05 (d, J=6.8 Hz, 3H).

Workup

  1. temperatureto warm to room temperature
  2. customquenched with 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts were dried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1)

Sources & evidence

ORD record
ord-1fac463ae16c490bb91b476bfa4fc554
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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