Sodium hydride → Allyl-pent-4-enyl-carbamic acid benzyl ester

HRID 751452Notes

Reaction equation

HRID 751452 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11](=[O:23])[N:12]([CH2:16][C:17]1C=C[CH:20]=[CH:19][CH:18]=1)[CH2:13][CH:14]=[CH2:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.BrCCCC=C>CN(C=O)C>[CH2:3]([O:10][C:11](=[O:23])[N:12]([CH2:13][CH:14]=[CH2:15])[CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-HCID 11277496benzyl N-benzyl-N-(prop-2-en-1-yl)carbamate

Product 1

HCID 10539222Allyl-pent-4-enyl-carbamic acid benzyl esterYield 104%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of NaH (1.83 g, 76.33 mmol of 90% NaH) in DMF was added benzyl allyl-carbamic acid benzyl ester (7.3 g, 38.2 mmol) in a dropwise fashion. The mixture was stirred at room temperature for approximately 10 minutes whereupon 5-bromo-1-pentene (6.78 mL, 57.24 mmol) was added in a dropwise fashion. The reaction was heated to 40° C. for approximately 4 hours whereupon the reaction was partitioned between dichloromethane and water. The organic layer was washed with water (2×'s), brine, dried (MgSO4), filtered and concentrated. Column chromatography of the residue (10% ethyl acetate:hexanes) provided 10.3 grams of the title compound as an oil: MS(EI) 260 (M+H+).

Workup

  1. additionwas added in a dropwise fashion
  2. customwas partitioned between dichloromethane and water
  3. washThe organic layer was washed with water (2×'s), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4be8ecd48000481f87cfb2b2cd83d2be
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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