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

HRID 238765ノート

反応式

HRID 238765 の反応式
[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]

参加物

4

反応物 2

HCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 178418336HCID 178418336、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-524901e7dfd64b698966664b8c91336e
出典データセット
uspto-grants-2014_02
特許番号
US08642576B2

反応ノート

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