Sodium hydride → HCID 11241613, compound

HRID 751451Notes

Reaction equation

HRID 751451 reaction equation
[H-].[Na+].[CH2:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=[CH2:5].Br[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]>CN(C=O)C>[C:9]([O:8][C:7](=[O:13])[N:6]([CH2:3][CH:4]=[CH2:5])[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-HCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamate

Product 1

HCID 11241613HCID 11241613, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of NaH (3.05 g, 76.33 mmol of 60% NaH in oil; washed with hexanes) in DMF (30 mL) was added tert-butyl N-allylcarbamate (6.0 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 2 hours whereupon the reaction was partitioned between ethyl acetate and water. The organic layer was washed with water (2×'s), brine, dried (MgSO4), filtered and concentrated to give 10 grams of the title compound as an oil: MS(EI) 226 (M+H+).

Workup

  1. additionwas added in a dropwise fashion
  2. customwas partitioned between ethyl acetate 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-470122b4afd243af80fbec5f74e4253b
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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