4-Fluoro-3-methoxybenzaldehyde → 1-(4-Fluoro-3-methoxyphenyl)-2-phenylethanol

HRID 238765

반응식

HRID 238765 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[CH2:12]([Mg]Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:10][CH3:11]

참가 물질

4

반응물 2

HCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 178418336HCID 178418336, 화합물

생성물 1

HCID 594588961-(4-Fluoro-3-methoxyphenyl)-2-phenylethanol수율 60.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
50 °C

실험 절차

To a solution of 4-fluoro-3-methoxybenzaldehyde (25 g, 162 mmol) in THF (150 mL) was added a solution of benzyl magnesium chloride (2 M solution in THF, 122 mL, 243 mmol) in THF (50 mL). The reaction mixture was heated at 50° C. for 2 h. The reaction mixture was allowed to cool to rt and quenched by addition of sat. NH4Cl. The reaction mixture was extracted with EtOAc (3×) and the combined organic layers were washed with sat. NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, eluting with 0-40% EtOAc/hexane) to yield 1-(4-fluoro-3-methoxyphenyl)-2-phenylethanol as a yellow oil (24 g, 60% yield). 1H NMR (500 MHz, CDCl3) δ ppm 7.27-7.32 (m, 2H), 7.21-7.27 (m, 1H), 7.16 (d, J=7 Hz, 2H), 7.01 (dd, J=11, 8 Hz, 1H), 6.92 (dd, J=8, 2 Hz, 1H), 6.82 (ddd, J=8, 4, 1 Hz, 1H), 4.80-4.88 (m, 1H), 4.66 (d, J=6 Hz, 1H), 3.84 (s, 3H), 2.91-3.04 (m, 2H).

후처리

  1. temperatureto cool to rt
  2. customquenched by addition of sat. NH4Cl
  3. extractionThe reaction mixture was extracted with EtOAc (3×)
  4. washthe combined organic layers were washed with sat. NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (SiO2, eluting with 0-40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-524901e7dfd64b698966664b8c91336e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642576B2

연결된 노트

불러오는 중…