Diethyl Ether → 2-(4-(Benzyloxy)phenyl)-2-(2-fluorophenyl)acetaldehyde

HRID 2174431ノート

反応式

HRID 2174431 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[F:46])[CH2:38][OH:39])=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)C>C(Cl)Cl>[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[F:46])[CH:38]=[O:39])=[CH:33][CH:32]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 712450572-(4-(Benzyloxy)phenyl)-2-(2-fluorophenyl)ethanol

生成物 1

HCID 894003632-(4-(Benzyloxy)phenyl)-2-(2-fluorophenyl)acetaldehyde収率 86.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Dess-Martin periodinane (5.38 g, 12.7 mmol) was suspended in CH2Cl2 (70 mL). Compound 3 (3.22 g, 10.0 mmol) dissolved in 20 mL CH2Cl2, was added under stirring. The resulting mixture was stirred overnight at room temperature. Diethyl ether (200 mL) was added and the organic phase was washed with NaOH (2×30 mL, 2M), NaHCO3 (50 mL, saturated aqueous solution), and brine (50 mL) and dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude material which was purified by column chromatography (heptane:ethyl acetate 4:1) to yield 2.76 g, 86% of 4 as a white solid. 1H-NMR (CDCl3) δ; 9.94 (dd, 1H, J=2.0 Hz and 1.5 Hz), 7.45-7.26 (m, 6H), 7.16 (d, 2H, J=8.6 Hz), 7.14-7.08 (m, 3H), 7.0 (d, 2H, J=9.0 Hz), 5.11 (ad, 1H, J=1.2 Hz), 5.07 (s, 2H); 13C-NMR (CDCl3) δ 197.6 (d, J=1.5 Hz), 160.7 (d, J=247 Hz), 158.5, 136.8, 130.5 (d, J=2.0 Hz), 130.5 (d, J=2.0 Hz), 129.3 (d, J=8.1 Hz), 128.6, 128.0, 127.4, 127.1, 124.4 (d, J=3.5 Hz), 115.7 (d, J=22.3 Hz), 115.5 (2C), 70.1, 57.1.

後処理

  1. additionwas added
  2. stirringThe resulting mixture was stirred overnight at room temperature
  3. washthe organic phase was washed with NaOH (2×30 mL, 2M), NaHCO3 (50 mL, saturated aqueous solution), and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation of the solvent under reduced pressure
  6. customgave a crude material which
  7. customwas purified by column chromatography (heptane:ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-17d839503177418f9325abbed2b2b90c
出典データセット
uspto-grants-2015_06
特許番号
US09061981B2

反応ノート

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