Thionyl Chloride → HCID 10873631, compound

HRID 1739038Notes

Reaction equation

HRID 1739038 reaction equation
O[CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].S(Cl)([Cl:33])=O>>[Cl:33][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 11080078HCID 11080078, compound

Product 1

HCID 10873631HCID 10873631, compoundYield 63%

Procedure

A mixture of ethyl 2-hydroxy-4-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butyrate (320 mg) and thionyl chloride (3 ml) was heated under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate-hexane (1:4, v/v) gave ethyl 2-chloro-4-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butyrate (210 mg, 63%) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washThe fractions eluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-a02c4a72bba348c286ed2093bbeaf2ea
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

Loading…