Dimethylformamide → HCID 66746261, compound

HRID 1175757Notes

Reaction equation

HRID 1175757 reaction equation
[C:1]12([CH2:9][CH:8](NC(NC3SC4C=C(C)C=CC=4N=3)=O)[C:7]3[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=3[O:5]1)[CH2:4][CH2:3][CH2:2]2.[CH:28]1(Br)C[CH2:31][CH2:30][CH2:29]1.[C:34]([O-:37])([O-])=O.[K+].[K+].CN(C=[O:44])C>>[CH:34]1([O:37][C:26]2[CH:25]=[CH:24][C:7]3[C:8](=[O:44])[CH2:9][C:1]4([O:5][C:6]=3[CH:27]=2)[CH2:2][CH2:3][CH2:4]4)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 16123366HCID 16123366, compound

Product 1

HCID 66746261HCID 66746261, compound

Conditions

Temperature
60 °C

Procedure

To a solution of 3,4-Dihydro-7-hydroxy-4-oxo-spiro[2H-1-benzopyran-2,1′-cyclobutane] (10 mmol) (from example 18) in DMF, cyclopentyl bromide (12 mmol) and K2CO3 (12 mmol) was added and the reaction mixture was heated at 60° C. for 12 h. Solvent was then evaporated and the residue was dissolved in ethyl acetate. Organic layer was washed with water, brine and separated. It was then dried on anhydrous Na2SO4 and concentrated to afford the desired product as oil.

Workup

  1. customSolvent was then evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washOrganic layer was washed with water, brine
  4. customseparated
  5. dry with materialIt was then dried on anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc55d41469cf4b9580d07e9ed24f9e03
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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