Triethylamine → 3-(2-Hydroxyethyl)phenethyl methanesulfonate

HRID 446368Notes

Reaction equation

HRID 446368 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([CH2:15][CH2:16][OH:17])[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][OH:14])[CH:7]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:17][CH2:16][CH2:15][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][OH:14])[CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 100807412-[3-(2-Hydroxyethyl)phenyl]ethanol

Product 1

HCID 581685333-(2-Hydroxyethyl)phenethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.67 mL) in DCM (2 mL) was added dropwise to a stirred solution at 0° C. of 2,2′-(1,3-phenylene)diethanol (1.30 g) and triethylamine (1.36 mL) in DCM (30 mL). The reaction mixture was stirred for 1 hour at 0° C. and then washed with water. The aqueous layer was re-extracted with DCM and the combined organic phases were dried, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 3% methanol in dichloromethane as solvent. Fractions containing the product were evaporated to dryness to afford the titled compound. Yield 0.52 g.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was re-extracted with DCM
  3. customthe combined organic phases were dried
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. additionFractions containing the product
  8. customwere evaporated to dryness

Sources & evidence

ORD record
ord-e5b6d89f30164207837c89940d50bb68
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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