Thionyl Chloride → HCID 21023608, compound

HRID 1795034Notes

Reaction equation

HRID 1795034 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:16][C@H:15]([CH2:17]O)[O:14][N:13]=2)=[CH:8][CH:7]=1>C(Cl)Cl>[Cl:3][CH2:17][C@@H:15]1[O:14][N:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 51674883HCID 51674883, compound

Product 1

HCID 21023608HCID 21023608, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.0 M in CH2Cl2, 6.0 ml, 6.0 mmol) was added dropwise to a solution of ((R)-3-(4-fluorophenyl)-4,5-dihydroisoxazol-5-yl)methanol (1.1 g, 5.6 mmol) in methylene chloride (10 ml) at 0° C. for 1 hour. Then the reaction mixture was allowed to warm to room temperature over 6 hours. The product was isolated and purified by removal of solvent under reduced pressure, followed by preparative chromatography (1:9 MeOH:CH2Cl2) to yield (5R)-5-(chloromethyl)-3-(4-fluorophenyl)-4,5-dihydroisoxazole (1.0 g, 4.8 mmol) as a colorless oil.

Workup

  1. customThe product was isolated
  2. custompurified by removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-00c2c7604e30443a8ad3e4707783c660
Source dataset
uspto-grants-2006_04
Patent number
US07026321B2

Reaction notes

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