Triethylamine → 3-(Diethoxymethyl)phenethyl methanesulfonate

HRID 1689242Notes

Reaction equation

HRID 1689242 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][CH:9]([O:19][CH2:20][CH3:21])[C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][OH:18])[CH:13]=[CH:14][CH:15]=1)[CH3:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:18][CH2:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:9]([O:8][CH2:6][CH3:7])[O:19][CH2:20][CH3:21])[CH:11]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 579893032-(3-(Diethoxymethyl)phenyl)ethanol

Product 1

HCID 579889463-(Diethoxymethyl)phenethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.18 g) in dichloromethane (0.2 mL) was added to a stirred solution of 2-(3-(diethoxymethyl)phenyl)ethanol (example 20, step c) (0.23 g) and triethylamine (0.429 mL) in dichloromethane (2.5 mL) cooled in an ice bath. After 1 h, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The ethyl acetate layer was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a gum. Yield 0.28 g.

Workup

  1. temperaturecooled in an ice bath
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. washThe ethyl acetate layer was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-bb54b6ae9446438cb7e07216b9ac11e0
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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