Triethylamine → 2-[(2-Methylpropan-2-yl)oxy]ethyl methanesulfonate

HRID 2230696Notes

Reaction equation

HRID 2230696 reaction equation
[C:1]([O:5][CH2:6][CH2:7][OH:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[S:17]([O:8][CH2:7][CH2:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:19])(=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 242322-(Tert-butoxy)ethan-1-olHCID 31297Methanesulfonyl chloride

Product 1

HCID 184649242-[(2-Methylpropan-2-yl)oxy]ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 2-t-butoxyethanol (3.37 g, 28.5 mmol), triethylamine (6 mL, 43 mmol), and dichloromethane (150 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (2.9 mL, 37.5 mmol). After 3 days, dilute the reaction mixture with dichloromethane and extract with a saturated solution of sodium bicarbonate and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 2-(t-butoxy)ethyl mesylate: Rf=0.75 (silica gel, 50% ethyl acetate/hexane).

Workup

  1. temperatureCool in an ice bath
  2. extractionextract with a saturated solution of sodium bicarbonate
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-7f4d7fd647474554b43faee6b2010de5
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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