Triethylamine → 3-Methoxypropyl methanesulfonate

HRID 660363Notes

Reaction equation

HRID 660363 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:14][S:15]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 741163-Methoxy-1-propanol

Product 1

HCID 116939633-Methoxypropyl methanesulfonateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-methoxy-propan-1-ol (300 g, 3.3 mol) in anhydrous CH2Cl2 (3 L) was added triethylamine (790 mL, 5.7 mol). The mixture was cooled to 0° C. and methanesulfonyl chloride (376 mL, 4.8 mol) in anhydrous CH2Cl2 (1 L) added dropwise. After stirring for 2 h at rt, the mixture was washed with water and brine, dried and evaporated to give the crude product as an oil (540 g, yield 96%) that was used in the next step without purification. 1H NMR (400 MHz, CDCl3): δ 3.40-3.37 (t, J=6.0 Hz, 2H), 2.55-2.52 (t, J=6.0 Hz, 2H), 2.40 (s, 3H), 2.06 (s, 3H), 1.08-1.02 (m, 2H).

Workup

  1. washthe mixture was washed with water and brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-48ac39509904488a81348829b7030e56
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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