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Triethylamine → 3-Dimethylcarbamoylpropyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionate

HRID 2419904
Notes
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Reaction equation

HRID 2419904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][O:13][C:14]([C:22]([F:25])([F:24])[F:23])([C:18]([F:21])([F:20])[F:19])[C:15](Cl)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH:28][CH2:29][CH2:30][CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]([C:18]([F:19])([F:20])[F:21])([C:22]([F:23])([F:24])[F:25])[C:15]([O:28][CH2:29][CH2:30][CH2:31][C:32](=[O:33])[N:34]([CH3:36])[CH3:35])=[O:16])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130008164-hydroxy-N,N-dimethylbutanamideHCID 203144652-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride

Product 1

HCID 203144693-Dimethylcarbamoylpropyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionateYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A solution of 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride (3.10 g.) in tetrahydrofuran (10 ml.) is added dropwise at 0° C. to a stirred mixture of 4-hydroxy-N,N-dimethylbutyramide (885 mg.), triethylamine (773 mg.) and tetrahydrofuran (15 ml.). The mixture is kept at room temperature for 4 hours with stirring, and for 2 days without stirring, then filtered. The filtrate is evaporated, and the residue dissolved in ether. The solution is washed with water, 0.4 N-aqueous sodium hydroxide, N-hydrochloric acid and water again, dried and evaporated to a syrup (3.3 g.). The syrup is dissolved in toluene (10 ml.) and applied to a column of silica gel (90 g.). The column is washed with toluene (700 ml.), and then eluted with ether (900 ml.). The ether is evaporated, and the residue is recrystallised from ether-light petroleum (b.p. 40-60° C.) to give 3-dimethylcarbamoylpropyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionate (2.1 g.), m.p. 54°-55° C.

Workup

  1. stirringfor 2 days without stirring
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. dissolutionthe residue dissolved in ether
  5. washThe solution is washed with water, 0.4 N-aqueous sodium hydroxide, N-hydrochloric acid and water again
  6. customdried
  7. customevaporated to a syrup (3.3 g.)
  8. dissolutionThe syrup is dissolved in toluene (10 ml.)
  9. washThe column is washed with toluene (700 ml.)
  10. washeluted with ether (900 ml.)
  11. customThe ether is evaporated
  12. customthe residue is recrystallised from ether-light petroleum (b.p. 40-60° C.)

Sources & evidence

ORD record
ord-f60855f637a445799c221f0449e2a715
Source dataset
uspto-grants-1978_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04107329

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes