Dichloromethane → 3-Methoxyphenyl 3-oxo-3-(3,4,5-trimethoxyphenyl)propanoate

HRID 529256Notes

Reaction equation

HRID 529256 reaction equation
[O:1]=[C:2]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH3:19][O:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=1.C(Cl)Cl>>[O:1]=[C:2]([C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)[CH2:3][C:4]([O:6][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([O:20][CH3:19])[CH:26]=1)=[O:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 90073-MethoxyphenolHCID 148497283-Oxo-3-(3,4,5-trimethoxyphenyl)propionic acid

Product 1

HCID 672867273-Methoxyphenyl 3-oxo-3-(3,4,5-trimethoxyphenyl)propanoateYield 49%

Procedure

To a mixture of 0.27 g (1.06 mmol) of the product of Step 1 and 0.13 g (1.06 mmol) of 3-methoxyphenol in 2 ml of anhydrous methylenechloride 0.16 ml (1.06 mmol) of diisopropylcarbondiimide was added at room temperature. The resulting mixture was stirred for 24 hours at room temperature and filtered off. The filtrate was evaporated to dryness and purified by flash column chromaytography (silica gel; methylene chloride) to give the title compound as a colorless crystals (0.185 g, 49%); 1H NMR (CDCl3) δ 3.77 (s, 3H, OMe); 3.91 (s, 6H, OMe); 4.17 (s, 3H, OMe); 4.173 (s, 2H, CH2); 6.6-6.8 (m, 3H, CH aromatic); 7.2-7.3 (m, 3H, CH aromatic).

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered off
  3. customThe filtrate was evaporated to dryness
  4. custompurified by flash column chromaytography (silica gel; methylene chloride)

Sources & evidence

ORD record
ord-118c6459ebe74b2b9f3d2f4a3066b811
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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