Borane → 3-(Furan-2-yl)propan-1-ol

HRID 76260

반응식

HRID 76260 반응식
[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]

참가 물질

4

반응물 2

HCID 6331BoraneHCID 702862-Furanpropionic acid

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-bf8a3094c84c47e28c70980942e125b2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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