Allyl bromide → HCID 53330780, compound

HRID 2042922Notes

Reaction equation

HRID 2042922 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])[C:5]([Cl:20])=[CH:4][C:3]=1[CH2:21][OH:22].[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27]>CN(C=O)C>[CH2:27]([O:22][CH2:21][C:3]1[C:2]([Br:1])=[CH:7][C:6]([CH2:8][O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:15])[CH3:16])=[C:5]([Cl:20])[CH:4]=1)[CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 53330279HCID 53330279, compound

Product 1

HCID 53330780HCID 53330780, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of alcohol 30 (31 g, 75.5 mmol) in DMF (300 mL) were added NaH (60% dispersion in mineral oil, 4.0 g, 98.2 mmol) at 0° C. The mixture was stirred at 0° C. for 15 min and allyl bromide (23 mL, 264 mmol) was added to the mixture at 0° C. The mixture was warmed up to room temperature and stirred at room temperature for 2 h. After dilution with water, the mixture was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 31 (32.1 g, 95%).

Workup

  1. temperatureThe mixture was warmed up to room temperature
  2. stirringstirred at room temperature for 2 h
  3. extractionAfter dilution with water, the mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-79ff8cca849145889a502d68d50efa45
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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