N-(2,3-Dimethyl-1-oxobutan-2-yl)-3-methoxy-2-methylbenzamide → N-[1-(hydroxy-m-tolyl-methyl)-1,2-dimethyl-propyl]-3-methoxy-2-methyl-benzamide

HRID 2223041Notes

Reaction equation

HRID 2223041 reaction equation
[CH:1]([C:3]([NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[CH3:18])([CH3:7])[CH:4]([CH3:6])[CH3:5])=[O:2].[CH3:20][C:21]1[CH:22]=[C:23]([Mg]Br)[CH:24]=[CH:25][CH:26]=1>C1COCC1>[OH:2][CH:1]([C:25]1[CH:26]=[C:21]([CH3:20])[CH:22]=[CH:23][CH:24]=1)[C:3]([NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[CH3:18])([CH3:7])[CH:4]([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 59713395N-(2,3-Dimethyl-1-oxobutan-2-yl)-3-methoxy-2-methylbenzamideHCID 178425413HCID 178425413, compound

Product 1

HCID 59713393N-[1-(hydroxy-m-tolyl-methyl)-1,2-dimethyl-propyl]-3-methoxy-2-methyl-benzamideYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried vial equipped with a stir bar was flushed with N2, charged with N-(1-formyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide (IX, R1=2-Me-3-MeO—Ph, R2=i-Pr, R3=Me, 131 mg, 0.5 mmol) in dry THF (1 mL) and cooled in dry ice acetone. 3-methylphenyl-magnesium bromide (1.0 M, 2 mL, 2.0 mmol) was added and the mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NaHCO3 (5 mL) and poured onto a 10 mL Chem Elut cartridge. After 5 min the cartridge was eluted with CH2Cl2 (25 mL). The eluate was evaporated to leave a secondary alcohol, N-[1-(hydroxy-m-tolyl-methyl)-1,2-dimethyl-propyl]-3-methoxy-2-methyl-benzamide (VIII, R1=2-Me-3-MeO—Ph, R2 =i-Pr, R3=Me, R4=3-Me—Ph, 180 mg). 1H and 13C NMR showed complete consumption of aldehyde.

Workup

  1. customAn oven-dried vial equipped with a stir bar
  2. customwas flushed with N2
  3. customThe reaction was quenched by addition of saturated aqueous NaHCO3 (5 mL)
  4. additionpoured onto a 10 mL Chem Elut cartridge
  5. washAfter 5 min the cartridge was eluted with CH2Cl2 (25 mL)
  6. customThe eluate was evaporated

Sources & evidence

ORD record
ord-bb12a37591f24c48978aed2d4fef53d6
Source dataset
uspto-grants-2008_05
Patent number
US07375093B2

Reaction notes

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