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Butyryl chloride → (+)-2-(4-(3-Butyryloxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

HRID 1163
Notes
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Reaction equation

HRID 1163 reaction equation
[OH:1][CH:2]([C:28]([F:31])([F:30])[F:29])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:7][CH:6]=1.[C:32](Cl)(=[O:36])[CH2:33][CH2:34][CH3:35]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:32]([O:1][CH:2]([C:28]([F:30])([F:31])[F:29])[CH:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:9][CH:10]=1)(=[O:36])[CH2:33][CH2:34][CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8855Butyryl chlorideHCID 54106197(-)-2-(4-(3-Hydroxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

Product 1

HCID 54507690(+)-2-(4-(3-Butyryloxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidineYield 93.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140Toluene
Solvent

Procedure

1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine. The solution was added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order, and then the toluene layer was concentrated under reduced pressure. The residue was purified by subjecting it to silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.08 g of (+)-2-(4-(3-butyryloxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxy-pyrimidine.

Workup

  1. washwashed with 4N hydrochloric acid, water
  2. concentrationa 5% sodium bicarbonate solution and water successively in that order, and then the toluene layer was concentrated under reduced pressure
  3. customThe residue was purified

Sources & evidence

ORD record
ord-a527bf234aeb411088cf0a7588b93b15
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723610

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes