Triethylamine → Benzyl 2-chloro-2-(3,4-dimethoxyphenyl)acetate

HRID 1667593Notes

Reaction equation

HRID 1667593 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11](O)[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.S([Cl:34])(C)(=O)=O>C(Cl)Cl>[Cl:34][CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57448185Benzyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetate

Product 1

HCID 57448186Benzyl 2-chloro-2-(3,4-dimethoxyphenyl)acetateYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6D (450 mg, 1.5 mmol) in CH2Cl2 (5 mL) at 0° C. was added triethylamine (0.42 mL, 3.0 mmol) followed by mesyl chloride (0.14 mL, 1.8 mmol). After stirring at rt overnight, the reaction was concentrated and purified via silica gel chromatography (0-25% ethyl acetate/hexanes) to provide 6E (268 mg, 56%). 1H NMR (400 MHz, CD3OD) δ ppm 3.81 (s, 3H) 3.87 (s, 3H) 5.19 (m, 2H) 5.36 (s, 1H) 6.81 (d, J=8.35 Hz, 1H) 6.93-7.07 (m, 2H) 7.20-7.42 (m, 5H).

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified via silica gel chromatography (0-25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f8b9b48b97ed4c2f9257011b29b07420
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

Loading…