Borane;tetrahydrofuran → N-[4-(hydroxymethyl)-3-methylphenyl]acetamide

HRID 2424626Notes

Reaction equation

HRID 2424626 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[C:7]([CH3:14])[CH:6]=1)(=[O:3])[CH3:2].B.C1COCC1>C1COCC1>[OH:10][CH2:9][C:8]1[CH:12]=[CH:13][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][C:7]=1[CH3:14]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27352244-Acetamido-2-methylbenzoic acid

Product 1

HCID 54053024N-[4-(hydroxymethyl)-3-methylphenyl]acetamideYield 20.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Acetylamino)-2-methylbenzoic acid (2 g, 10.4 mmol) was suspended in THF (50 mL) and borane-THF complex (1M in THF, 26 mL, 26 mmol) added drop-wise over 15 minutes. The reaction mixture was stirred under argon overnight. The reaction mixture was quenched with water (51 mL) and extracted with EtOAc (×3). The combined organics were dried and concentrated. The crude product was purified by chromatography. Elution with 0-100% EtOAc/petroleum ether yielded the title compound as a cream solid (0.379 g). δH (MeOD, 400 MHz) 7.36 (2H, d), 7.25 (1H, d), 4.57 (2H, s), 2.31 (3H, s), 2.10 (3H, s). MS (ES+): MH+ 180.2.

Workup

  1. customThe reaction mixture was quenched with water (51 mL)
  2. extractionextracted with EtOAc (×3)
  3. customThe combined organics were dried
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography
  6. washElution with 0-100% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-0b17c7b79226439eb7851caf876355aa
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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