3-Methoxybenzyl chloride → 1-(4-Iodophenyl)-3-(3-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-one

HRID 534245Notes

Reaction equation

HRID 534245 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[I:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:28])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:14][CH:13]=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34]Cl>C1COCC1>[I:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:28])[CH:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[C:31]([O:30][CH3:29])[CH:32]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 699943-Methoxybenzyl chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 433382141-(4-Iodophenyl)-2-(4-methoxyphenyl)ethanone

Product 1

HCID 680001051-(4-Iodophenyl)-3-(3-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-oneYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium bis(trimethylsilyl)amide (2.5 g, 12.5 mmol) was added to a solution of 1-(4-iodophenyl)-2-(4-methoxyphenyl)ethanone (4.225 g, 12.00 mmol) and THF (60 mL) at rt under N2. After 3.5 h, 3-methoxybenzyl chloride (2.2 mL, 15 mmol) was added. After 2.5 days, the reaction was quenched with saturated aqueous ammonium chloride solution (100 mL) and extracted with ethyl acetate (150 mL). The ethyl acetate extract was dried (MgSO4), filtered, concentrated, and purified by silica gel chromatography (99:1→4:1; hexanes:ethyl acetate) to give 4.7 g of 1-(4-iodophenyl)-3-(3-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-one as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.83 (d, 2H), 7.76 (d, 2H), 7.20 (d, 2H), 7.09 (t, 1H), 6.81 (d, 2H), 6.76-6.65 (m, 3H), 5.13 (t, 1H), 3.67 (s, 3H), 3.66 (s, 3H), 3.35 (dd, 1H), 2.93 (dd, 1H).

Workup

  1. waitAfter 2.5 days
  2. customthe reaction was quenched with saturated aqueous ammonium chloride solution (100 mL)
  3. extractionextracted with ethyl acetate (150 mL)
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (99:1→4:1; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-3e874782d8194e0598365bc3d3c7c8a7
Source dataset
uspto-grants-2014_10
Patent number
US08853423B2

Reaction notes

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