Triethylamine → Methanesulfonic acid 2-benzo[d]isoxazol-3-yl-ethyl ester

HRID 1992396Notes

Reaction equation

HRID 1992396 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][OH:12])=[N:2]1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][O:12][S:21]([CH3:20])(=[O:23])=[O:22])=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 122791422-(BENZO[D]ISOXAZOL-3-YL)ETHANOL

Product 1

HCID 86625996Methanesulfonic acid 2-benzo[d]isoxazol-3-yl-ethyl esterYield 103.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-benzo[d]isoxazol-3-yl-ethanol (0.537 g, 3.29 mmol, from step (i) above ) and triethylamine (0.55 mL, 3.95 mmol) in dichloromethane (20 mL) was added methanesulfonyl chloride (0.31 mL, 3.95 mmol) at 0° C. The reaction mixture was stirred for 1 hour and was then extracted with water (2×20 mL) and brine (20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo, which afforded 818 mg (98%) of the title compound.

Workup

  1. extractionwas then extracted with water (2×20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo, which

Sources & evidence

ORD record
ord-6468d0427128410da12af6a3e2a74490
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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