Triethylamine → Methyl [4-(3-methanesulfonyloxypropyl)phenoxy]acetate

HRID 1700945Notes

Reaction equation

HRID 1700945 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22949949Methyl [4-(3-hydroxypropyl)phenoxy]acetate

Product 1

HCID 22949950Methyl [4-(3-methanesulfonyloxypropyl)phenoxy]acetateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl [4-(3-hydroxypropyl)phenoxy]acetate (4.5 g, 20.5 mmol) in dichloromethane (50 ml) was treated at 0° C. with triethylamine (4.36 g, 43.1 mmol) followed by methanesulfonyl chloride (3.99 g, 34.8 mmol) added dropwise over 5 min. After 30 min at 0° C., the reaction mixture was diluted with dichloromethane, washed with 1N hydrochloric acid, water and dried over anhydrous sodium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 8:18) gave 5.51 g (89%) of the title material as a white solid: mp 49-51° C.

Workup

  1. additionadded dropwise over 5 min
  2. washwashed with 1N hydrochloric acid, water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 8:18)

Sources & evidence

ORD record
ord-3738c5ec6158472393c6b0833dd9c065
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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