Triethylamine → 3,4-Methylenedioxyphenethyl mesylate

HRID 456587Notes

Reaction equation

HRID 456587 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-ol

Product 1

HCID 186255853,4-Methylenedioxyphenethyl mesylateYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol (a) (1.90 g, 11 mmol) in dichloromethane (25 ml) was treated at 0° C. with triethylamine (1.9 ml, 13.7 mmol) and methanesulfonyl chloride (1.1 ml, 13.7 mmol). After 1.5 hours at room temperature the mixture was partitioned between dichloromethane and water. The organic extract was dried and evaporated to give a yellow oil (2.7 g, 96%).

Workup

  1. customAfter 1.5 hours at room temperature the mixture was partitioned between dichloromethane and water
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated

Sources & evidence

ORD record
ord-411bf821d8784d468f227ada430abb2a
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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