3-(3,4-Dichlorophenyl)propionic acid → 3-(3,4-Dichlorophenyl)propan-1-ol

HRID 1848384

반응식

HRID 1848384 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

4

반응물 2

HCID 1411813-(3,4-Dichlorophenyl)propionic acidHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 190753133-(3,4-Dichlorophenyl)propan-1-ol수율 107.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

At rt to a suspension of 3-(3,4-dichlorophenyl)propanoic acid (2.0 g, 9.1 mmol) in THF (40 mL) was added borane-THF (18.3 mL, 1.00M in THF, 18.3 mmol). After 12 h, the reaction mixture was cooled to 0° C. and quenched by the cautious addition of 1M NaOH. The reaction mixture was diluted with ether, washed with water twice, then brine, and the organic portion dried over MgSO4, filtered, and concentrated. Trituration with 10% Ethyl acetate/Hexane (300 mL) gave a white powder which was collected by filtration to give Intermediate 17A (2.00 g, 9.80 mmol, 100% crude). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.73-1.81 (2H, m), 2.56-2.65 (2H, m), 3.59 (2H, t, J=6.4 Hz), 6.96 (1H, dd, J=8.0, 2.0 Hz), 7.22 (1H, d, J=2.0 Hz), 7.27 (1H, d, J=8.3 Hz).

후처리

  1. customquenched by the cautious addition of 1M NaOH
  2. additionThe reaction mixture was diluted with ether
  3. washwashed with water twice
  4. dry with materialbrine, and the organic portion dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customTrituration with 10% Ethyl acetate/Hexane (300 mL) gave a white powder which
  8. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-915258dcd3a24caba6b510d3ca310d8c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952180B2

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