Water → HCID 57305844, compound

HRID 727193Notes

Reaction equation

HRID 727193 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([C:13]3[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:23][OH:24])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[C:25]1([CH2:31]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>C1(C)C=CC=CC=1>[O:3]1[C:7]2([CH2:8][CH2:9][CH:10]([C:13]3[C:18]([C:19]([F:21])([F:20])[F:22])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:23][O:24][CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:11][CH2:12]2)[O:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19705272HCID 19705272, compound

Product 1

HCID 57305844HCID 57305844, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A suspension of 3.3 grams (0.084 mole) of sodium hydride (60% in mineral oil) in 20 mL of toluene is stirred, and a solution of 24.3 grams (0.080 mole) of [(1,4-dioxaspiro[4.5]decan-8-yl)(3-trifluoromethylphenyl)]methanol in 65 mL of toluene is added dropwise. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about one hour. After this time a solution of 13.7 grams (0.080 mole) of phenylmethyl bromide in 45 mL of toluene is added dropwise. Upon completion of addition, the reaction mixture is heated to reflux where it is stirred for about 4 hours. The reaction mixture is then cooled and shaken with water. The organic layer is separated and dried with magnesium sulfate. The mixture is filtered and the filtrate is concentrated under reduced pressure, yielding phenylmethyl [(1,4-dioxaspiro[4.5]decan-8-yl)(3-trifluoromethylphenyl)]methyl ether.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture is stirred at ambient temperature for about one hour
  3. additionUpon completion of addition
  4. temperaturethe reaction mixture is heated
  5. temperatureto reflux where it
  6. stirringis stirred for about 4 hours
  7. temperatureThe reaction mixture is then cooled
  8. customThe organic layer is separated
  9. dry with materialdried with magnesium sulfate
  10. filtrationThe mixture is filtered
  11. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3f1a0e41ca64c7ca8ce9e3c48b255b7
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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