Triethylamine → Ethyl 3-[4-(chloromethyl)phenyl]propanoate

HRID 2218119Notes

Reaction equation

HRID 2218119 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=1)[CH3:2].C(N(CC)CC)C.S([Cl:27])(C)(=O)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Cl:27])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14839455Ethyl 3-(4-(hydroxymethyl)phenyl)propanoate

Product 1

HCID 11107077Ethyl 3-[4-(chloromethyl)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(4-hydroxymethylphenyl)propionic acid ethyl ester (P5, 2.9 g, 13.9 mmol) in triethylamine (4.0 mL, 27.8 mmol) and dichloromethane (30 mL) was slowly added at 0° C. mesyl chloride (1.6 mL, 20.9 mmol). The solution was stirred at room temperature for 18 hours, then the solution was washed with 1N aqueous hydrochloric acid. The organic phase was dried (anhydrous magnesium sulfate) and concentrated to afford the title compound as an oil.

Workup

  1. washthe solution was washed with 1N aqueous hydrochloric acid
  2. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9f339144f51a43809f4712a0b5b4a872
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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