Triethylamine → 2-(5-Methanesulfonyloxymethyl-isoxazol-3-yl)-pyridine

HRID 707642Notes

Reaction equation

HRID 707642 reaction equation
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:4]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:4]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6865423-(2-Pyridinyl)-5-isoxazolemethanol

Product 1

HCID 867068402-(5-Methanesulfonyloxymethyl-isoxazol-3-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-(5-hydroxymethyl-isoxazol-3-yl)-pyridine (4.0 gm), and triethylamine (6.5 ml) in dichloromethane (40 ml) was added methanesulfonyl chloride (2.8 ml) at 0° C. The reaction mixture was stirred at 0° C. over a period of 1 h. The reaction was quenched by addition of water and layers were separated. Aqueous layer was extracted with dichloromethane (40 ml×2). Combined organic layer was washed with aqueous sodium bicarbonate solution followed by water and evaporated under vacuum to provide the title compound in 5.1 gm quantity (84%) as a semisolid, which was used without purification for the next reaction.

Workup

  1. customThe reaction was quenched by addition of water and layers
  2. customwere separated
  3. extractionAqueous layer was extracted with dichloromethane (40 ml×2)
  4. washCombined organic layer was washed with aqueous sodium bicarbonate solution
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-9443767c32f349dababd96366b409d9e
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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