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

HRID 1060229

反応式

HRID 1060229 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 3567085(2-Methyl-5-nitrophenyl)methanol収率 95.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6a4e6d6f47e94bbd8cef11feb56f19bf
出典データセット
uspto-grants-2003_02
特許番号
US06521663B2

関連ノート

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