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

HRID 2174431Notes

Reaction equation

HRID 2174431 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-17d839503177418f9325abbed2b2b90c
Source dataset
uspto-grants-2015_06
Patent number
US09061981B2

Reaction notes

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