Water → HCID 14346530, compound

HRID 1493746Notes

Reaction equation

HRID 1493746 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7]([C:9]1[C:14]([OH:15])=[C:13](O)[CH:12]=[CH:11][C:10]=1[CH2:17][C:18]#[N:19])[CH3:8].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:7]([C:9]1[C:14]([O:15][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:13]([O:4][CH2:1][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:12]=[CH:11][C:10]=1[CH2:17][C:18]#[N:19])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14346529HCID 14346529, compound

Product 1

HCID 14346530HCID 14346530, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid potassium carbonate (1.94 g) was added at room temperature to a solution of the product from stage (i) (1 g) in dry dimethylformamide. Benzyl bromide (2.41 g) was added. The mixture was stirred overnight. Ice and water were added. The mixture was extracted with ether. The extracts were washed with water, dried and evaporated. The oil obtained was purified by FCC using ether/hexane (1:1) as eluent, to give the title compound as a yellow oil which crystallised slowly (1.82 g) m.p. 44°-47.5°.

Workup

  1. extractionThe mixture was extracted with ether
  2. washThe extracts were washed with water
  3. customdried
  4. customevaporated
  5. customThe oil obtained
  6. customwas purified by FCC

Sources & evidence

ORD record
ord-c5abf8caa449441b96408e39fd6dc68d
Source dataset
uspto-grants-1991_06
Patent number
US05023378

Reaction notes

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