Benzyl Bromide → HCID 77374747, compound

HRID 1085921Notes

Reaction equation

HRID 1085921 reaction equation
[CH:1]([OH:8])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:1]([CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][CH2:12][O:8][CH2:1][CH3:2]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 71349956HCID 71349956, compound

Product 1

HCID 77374747HCID 77374747, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.9 g of the alcohol 3, 1.68 g of sodium hydride, 300 mg of tetrabutylammonium iodide and 5.95 g of benzyl bromide in 250 ml of THF was stirred for 4 hours at 60° C. At the end of this time 100 ml of saturated aqueous ammonium chloride solution was added and the mixture extracted with 200 ml of EtOAc and the organic phase was dried with sodium sulfate. Concentration under vacuum provided the title compound.

Workup

  1. extractionthe mixture extracted with 200 ml of EtOAc
  2. dry with materialthe organic phase was dried with sodium sulfate
  3. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-7897477544db4426bf061ef729688ac2
Source dataset
uspto-grants-1991_04
Patent number
US05011943

Reaction notes

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