Borane → (2-Methyl-5-nitrophenyl)methanol

HRID 2184211

반응식

HRID 2184211 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].B.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH2:4][OH:5]

참가 물질

6

반응물 3

HCID 6331BoraneHCID 11430Potassium CarbonateHCID 5196832-Methyl-5-nitrobenzoic acid

생성물 1

HCID 3567085(2-Methyl-5-nitrophenyl)methanol수율 95.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

2-Methyl-5-nitrobenzoic acid (2.00 g, 11.0 mmol) was warmed under nitrogen, dissolved in anhydrous THF (25 mL), and treated with a 1N solution of borane in THF (16.5 mL). After stirring 18 hours at ambient temperature the reaction was quenched with a solution of potassium carbonate (1.8 g, 13 mmol) in water (50 mL), and the THF removed in vacuo. The remaining aqueous solution was extracted with DCM, and the organic layer washed with pH 7 buffer and brine, dried over sodium sulfate, and filtered. The evaporated filtrate gave the title compound as a pale yellow solid (1.76 g, 95%). 1H NMR (300 MHz, CDCl3) δ 8.29 (d, 1H, J=2.5 Hz), 8.04 (dd, 1H, J=8.3 Hz, 2.5 Hz), 7.31 (d, 1H, J=8.31 Hz), 4.77 (d, 2H, J=5.5 Hz), 2.41 (s, 3H), 2.09 (t, 1H, J 5.6 Hz).

후처리

  1. customthe THF removed in vacuo
  2. extractionThe remaining aqueous solution was extracted with DCM
  3. washthe organic layer washed with pH 7 buffer
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-c5b88d121e2e44029ae58041f92e0a19
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900231B2

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