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

HRID 2174431노트

반응식

HRID 2174431 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-17d839503177418f9325abbed2b2b90c
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061981B2

반응 노트

불러오는 중…