Sodium hydride → HCID 178448049, compound

HRID 989584Notes

Reaction equation

HRID 989584 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11].Br[CH2:13][CH2:14][CH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C@H:22]2[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]2)[CH2:18][CH2:17]1>CN(C=O)C.O.CN(C=O)C.C1(C)C=CC=CC=1>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:30][CH2:29][CH2:28][C@H:25]1[CH2:26][CH2:27][C@H:22]([C@H:19]2[CH2:18][CH2:17][C@H:16]([CH2:15][CH2:14][CH3:13])[CH2:21][CH2:20]2)[CH2:23][CH2:24]1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 808792,3-DifluorophenolHCID 178448041HCID 178448041, compound

Product 1

HCID 178448049HCID 178448049, compoundYield 56.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×HCID 21735183Dimethylformamide tolueneSolvent

Procedure

Under nitrogen gas stream, 29.8 g (683 mmol) of 55% sodium hydride was added to 100 ml of DMF and cooled with water, a solution of 74.0 g (569 mmol) of 2,3-difluorophenol in 700 ml of DMF was added by drops thereto, and they were stirred for 1 hour. To the reaction mixture was added by drops a solution of 156 g (474 mmol) of the crude 1-bromo-3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propane in 400 ml of mixed solvent of DMF/toluene (3/1), and then they were stirred at 80° C. for 3 hours. The reaction mixture was added to 500 ml of water to terminate the reaction, and the organic layer was separated, washed with 500 ml of water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: heptane) and recrystallized from heptane to obtain 101 g of 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propyl 2,3-difluorophenyl ether.

Workup

  1. stirringthey were stirred at 80° C. for 3 hours
  2. customto terminate
  3. customthe reaction
  4. customthe organic layer was separated
  5. washwashed with 500 ml of water thrice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under a reduced pressure
  8. customrecrystallized from heptane

Sources & evidence

ORD record
ord-d34a3a88c2714e89ad1f73d9e682cadb
Source dataset
uspto-grants-2002_10
Patent number
US06458433B1

Reaction notes

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