Thionyl Chloride → Isoxazole, 4-(chloromethyl)-5-methyl-3-phenyl-

HRID 1521145Notes

Reaction equation

HRID 1521145 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13]O.S(Cl)([Cl:17])=O>ClCCl.O>[Cl:17][CH2:13][C:3]1[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][O:6][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 11052826Isoxazole, 4-(chloromethyl)-5-methyl-3-phenyl-Yield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (4.5 g, 236 mmol) in dichloromethane (50 mL) was added at 0° C. thionyl chloride (3.6 g, 2.7 mL, 306 mmol) dropwise over 3 min and the solution stirred at 0° C. for 2 h. After this time, the mixture was diluted with water (50 mL) and the organic phase separated and washed with brine. The aqueous phase was extracted with dichloromethane and the combined extracts dried over sodium sulfate, filtered and evaporated to afford the title compound (4.6 g, 93%) which was obtained as a light brown liquid. MS: m/e=208.1 [M+H]+.

Workup

  1. customthe organic phase separated
  2. washwashed with brine
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined extracts dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-cd890240d81240e985ba5e014672378b
Source dataset
uspto-grants-2015_07
Patent number
US09073908B2

Reaction notes

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