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Water → (-)-2-(4-(4-Octyloxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine

HRID 1735983
Notes
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Reaction equation

HRID 1735983 reaction equation
[OH:1][CH:2]([C:29]([F:32])([F:31])[F:30])[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:14][N:13]=2)=[CH:8][CH:7]=1.[H-].[K+].C1(C)C=CC(S(O[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])(=O)=O)=CC=1.O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:45]([O:1][CH:2]([C:29]([F:31])([F:32])[F:30])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:14][N:13]=2)=[CH:10][CH:11]=1)[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 82127Potassium hydrideHCID 599296n-Octyl p-ToluenesulfonateHCID 19694914(-)-2-(4-(4-Hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine

Product 1

HCID 19435043(-)-2-(4-(4-Octyloxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidineYield 56.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.1 g (2.5 mmol) of (-)-2-(4-(4-hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine was dissolved in 10 ml of tetrahydrofuran. This solution was added with 0.12 g (3 mmol) of potassium hydride, stirred at 10°-20° C. for 20 minutes, further added with 0.85 g (3 mmol) of octyl p-toluenesulfonate and reacted at 20°-30° C. for 2 hours. The reaction mixture was poured into 100 ml of water and 100 ml of toluene, and the toluene layer was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 0.80 g of (-)-2-(4-(4-octyloxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine

Workup

  1. customreacted at 20°-30° C. for 2 hours
  2. washthe toluene layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1789afb5355746d8aebc00d8001c9cc7
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05539115

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes