Borane → 3-(Furan-2-yl)propan-1-ol

HRID 76260

反応式

HRID 76260 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8](O)=[O:9].B>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9]

参加物

4

反応物 2

HCID 6331BoraneHCID 702862-Furanpropionic acid

生成物 1

HCID 2271783-(Furan-2-yl)propan-1-ol収率 79.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 3-(furan-2-yl)propanoic acid (1.4 g, 10 mmol) in THF (50 mL) was added dropwise borane (1M) (20 mL, 20 mmol). The mixture was stirred at rt for 12 hrs, quenched with MeOH, and the mixture was concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.0 g (79%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.87-1.94 (m, 2 H) 2.74 (t, J=7.32 Hz, 2 H) 3.69 (t, J=6.10 Hz, 2 H) 6.28 (dd, J=3.05, 1.83 Hz, 1 H) 7.30 (d, J=0.92 Hz, 1 H).

後処理

  1. customquenched with MeOH
  2. concentrationthe mixture was concentrated
  3. customThe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-bf8a3094c84c47e28c70980942e125b2
出典データセット
uspto-grants-2014_09
特許番号
US08835475B2

関連ノート

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