Hydride → 3,5-Dichloro-4-(4-methoxyphenoxy)benzyl Alcohol

HRID 1168090

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HRID 1168090 반응식
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:7]([Cl:21])[CH:6]=1)C.[H-]>ClCCl>[Cl:11][C:9]1[CH:10]=[C:5]([CH2:4][OH:3])[CH:6]=[C:7]([Cl:21])[C:8]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1

참가 물질

4

반응물 2

HCID 166653HydrideHCID 697553463,5-Dichloro-4-(4-methoxy-phenoxy)-benzoic acid ethyl ester

생성물 1

HCID 222856543,5-Dichloro-4-(4-methoxyphenoxy)benzyl Alcohol수율 72.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3,5-dichloro-4-(4-methoxy-phenoxy)-benzoic acid ethyl ester (1.36 g, 4.01 mmol) in dichloromethane (35 ml) at 0° C. was added diisobutylaluminun hydride (1M in toluene, 12 ml, 12 mmol) and the mixture was stirred for 2.5 hours at 0° C. The reaction mixture was quenched with potassium sodium tartrate tetrahydrate (0.5 M aqueous solution, 50 ml), stirred for 20 minutes at room temperature and then was filtered through diatomaceous earth. The filtrate was concentrated and then taken up in water (60 ml). The aqueous solution was extracted with ethyl acetate (4×60 ml). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane) to afford the title compound (871 mg). NMR (400 MHz, CDCl3) δ7.39 (s, 2H), 6.74-6.82 (m, 4H), 4.69 (d, 2H), 3.76 (s, 3H), 1.83 (t, 1 H).

후처리

  1. customThe reaction mixture was quenched with potassium sodium tartrate tetrahydrate (0.5 M aqueous solution, 50 ml)
  2. stirringstirred for 20 minutes at room temperature
  3. filtrationwas filtered through diatomaceous earth
  4. concentrationThe filtrate was concentrated
  5. extractionThe aqueous solution was extracted with ethyl acetate (4×60 ml)
  6. customThe combined extracts were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-0133d51d904c4f07ad48b04650104254
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620830B2

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