Sodium hydride → HCID 67146001, compound

HRID 2422263Notes

Reaction equation

HRID 2422263 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>CN(C)C=O.C(OCC)(=O)C>[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 1211242451458-31-2

Product 1

HCID 67146001HCID 67146001, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution (100 mL) of tert-butyl 3-(4-hydroxyphenyl)propanoate (5.5 g, 24.7 mmol) in N,N-dimethylformamide was added 60% sodium hydride (1.09 g, 27.2 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 15 min. Then, 3-bromobenzylbromide (6.55 g, 25.91 mmol) was added to this mixture with stirring at 0° C., and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was diluted with ethyl acetate, and washed with water and saturated brine. The ethyl acetate layer was dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (7.5 g, yield 78%) as a colorless powder.

Workup

  1. stirringthe mixture was stirred at the same temperature for 15 min
  2. stirringwith stirring at 0° C.
  3. stirringthe mixture was stirred at room temperature for 12 hrs
  4. washwashed with water and saturated brine
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb9f75ea69b74d83a9a8f331b5158f16
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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