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

HRID 883792노트

반응식

HRID 883792 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 EtOAc (×3). The combined organics were dried and concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% EtOAc/petroleum ether yielded the title compound as a cream solid (0.379 g). δH (CD3OD, 400 MHz) 7.36 (2H, d), 7.25 (1H, d), 4.57 (2H, s), 2.31 (3H, s), 2.10 (3H, s). MH+ 180.2.

후처리

  1. customthen quenched with water (52 ml)
  2. extractionextracted with EtOAc (×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% EtOAc/petroleum ether

출처 및 근거

ORD 기록
ord-694ed6b3095740efb973fa237c32a294
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236953B2

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