Dimethylformamide → HCID 19428153, compound

HRID 1078606Notes

Reaction equation

HRID 1078606 reaction equation
O[C:2]1[C:7]2[C:8]([CH3:16])=[C:9]([CH2:13][CH2:14][OH:15])[C:10](=O)[O:11][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1.[C:18](=[O:21])(O)[O-:19].[K+].[CH2:23](I)[CH3:24].[CH3:26]N(C=O)C>>[CH2:10]([O:11][C:6]1[C:7]2[C:8]([CH3:16])=[C:9]([CH2:13][CH2:14][OH:15])[C:18](=[O:21])[O:19][C:2]=2[CH:3]=[C:4]([O:17][CH2:23][CH3:24])[CH:5]=1)[CH3:26]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 516893Potassium BicarbonateHCID 19428162HCID 19428162, compound

Product 1

HCID 19428153HCID 19428153, compound

Procedure

33.0 g (140 mmol) of 5,7-dihydroxy-3-(2-hydroxyethyl)-4-methyl-2H-1-benzopyran-2-one (Example 49), 56.0 g (560 mmol) of potassium bicarbonate and 76.4 g (490 mmol) of ethyl iodide are stirred in 500 ml of DMF for 55 hours at 80° C. under nitrogen. The solution is evaporated, extracted with chloroform, and the organic phase is washed with dilute sodium hydroxide and with water, dried with Na2SO4 and re-evaporated. The product is purified by column chromatography over silica gel 60 (eluent: ethylacetate/acetone). Yield 19.5 g (48%); m.p. 117°-119° C. (from acetone/petroleum ether).

Workup

  1. customThe solution is evaporated
  2. extractionextracted with chloroform
  3. washthe organic phase is washed with dilute sodium hydroxide and with water
  4. dry with materialdried with Na2SO4
  5. customre-evaporated
  6. customThe product is purified by column chromatography over silica gel 60 (eluent: ethylacetate/acetone)

Sources & evidence

ORD record
ord-cf6d60cce97c495d87ba300e52d22a55
Source dataset
uspto-grants-1996_08
Patent number
US05550129

Reaction notes

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