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

HRID 228378Notes

Reaction equation

HRID 228378 reaction equation
C(N(CC)CC)C.[C:8]([O:12][CH2:13][CH2:14][OH:15])([CH3:11])([CH3:10])[CH3:9].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:15][CH2:14][CH2:13][O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:19])=[O:18]

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

At 0° C. add triethylamine (35.4 mL, 254 mmol) to a stirring solution of 2-tert-butoxyethanol (10.0 g, 84.6 mmol) and methanesulfonic chloride (13.1 mL, 169 mmol) in dichloromethane (169 mL). Allow the reaction mixture to warm to room temperature over night. Dilute the reaction mixture with dichloromethane (200 mL) and wash it with water (1×100 mL), 1.0 N HCl (1×100 mL) and 1.0 N NaOH (1×100 mL). Dry the organic layer over MgSO4, filter and concentrate to give the title compound: 1H NMR (CHCl3-d6) 4.33 (t, 2H), 3.62 (t, 2H), 3.06 (s, 3H), 1.21 (s, 9H) GC/MS, tR 13.7 min, % of total 92.9%.

Workup

  1. washwash it with water (1×100 mL), 1.0 N HCl (1×100 mL) and 1.0 N NaOH (1×100 mL)
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-41a71416005c42f299b4ca256bc27657
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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