Triethylamine → Methanesulfonic acid 3,4-dimethoxy-5-propylbenzyl ester

HRID 638912Notes

Reaction equation

HRID 638912 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=1[O:11][CH3:12])[CH2:6][OH:7].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=1[O:11][CH3:12])[CH2:6][O:7][S:24]([CH3:23])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19838159(3,4-Dimethoxy-5-propylphenyl)methanol

Product 1

HCID 86618866Methanesulfonic acid 3,4-dimethoxy-5-propylbenzyl esterYield 51.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,4-dimethoxy-5-propylbenzylalcohol (171 mg, 0.82 mmol) in CH2Cl2 (5.0 mL) at room temperature was added triethylamine (0.23 mL, 1.63 mmol) followed by methanesulfonyl chloride (95 μL, 1.22 mmol, 1.5 eq.). After 30 min the reaction mixture was diluted with hexanes (20 mL) and filtered through a pad of silica gel. The pad was then washed with 25% EtOAc in hexanes (100 mL). The combined organic filtrate was then concentrated to give methanesulfonic acid 3,4-dimethoxy-5-propylbenzyl ester (122 mg) as oil, which was used without further purification.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. washThe pad was then washed with 25% EtOAc in hexanes (100 mL)
  3. concentrationThe combined organic filtrate was then concentrated

Sources & evidence

ORD record
ord-a149b92331534b3db5194043bf35ba52
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

Loading…