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

HRID 534759Notes

Reaction equation

HRID 534759 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 at room temperature overnight then quenched with water (52 mL) and extracted with ethyl acetate (×3). The combined organics were dried and concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% ethyl acetate/petroleum ether yielded the title compound as a cream solid (0.379 g). δH (MeOD, 400 MHz) 7.36 (2H, m), 7.25 (1H, d), 4.57 (2H, s), 2.31 (3H, s), 2.10 (3H, s). MS (ES): MH+ 180.2.

Workup

  1. customthen quenched with water (52 mL)
  2. extractionextracted with ethyl acetate (×3)
  3. customThe combined organics were dried
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography
  7. washElution with 0-100% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-10a7e209ff7d421189a491c5d9c4f99e
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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