2-Bromopropane → HCID 19428133, compound

HRID 1078603Notes

Reaction equation

HRID 1078603 reaction equation
[OH:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([CH2:12][CH2:13][OH:14])=[C:7]([CH3:15])[C:6]=2[CH:16]=1.[H-].[Na+].Br[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[OH:14][CH2:13][CH2:12][C:8]1[C:9](=[O:11])[O:10][C:5]2[CH:4]=[C:3]([O:17][CH3:18])[C:2]([O:1][CH:22]([CH3:24])[CH3:23])=[CH:16][C:6]=2[C:7]=1[CH3:15]

Participants

5

Reactant 3

HCID 63582-Bromopropane2×HCID 24758Sodium hydride2×HCID 19428152HCID 19428152, compound

Product 1

HCID 19428133HCID 19428133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

67 g (268 mmol) of 6-hydroxy-3-(2-hydroxyethyl)-7-methoxy-4-methyl-2H-1-benzopyran-2-one (Example 41) is carefully added, using an ice bath for cooling, to 11.8 g (295 mmol) of sodium hydride (60% in white oil) in 300 ml of DMF. The mixture is stirred for 1 hour at room temperature, and then 49.5 g (402 mmol) of 2-bromopropane is added dropwise and the mixture is stirred for 24 hours at 60° C. under nitrogen. After adding a further 3.33 g (83 mmol) of sodium hydride and 52.4 g (426 mmol) of 2-bromopropane, the mixture is stirred for a further 24 hours at 60° C. The solution is evaporated, extracted with ethyl acetate, and the organic phase is washed with water, dried with Na2SO4 and re-evaporated. The product is purified by column chromatography over silica gel 60 (eluent: ethyl acetate). Yield 53.3 g (68%); m.p. 110°-112° C. (from acetone/PE).

Workup

  1. stirringthe mixture is stirred for 24 hours at 60° C. under nitrogen
  2. stirringthe mixture is stirred for a further 24 hours at 60° C
  3. customThe solution is evaporated
  4. extractionextracted with ethyl acetate
  5. washthe organic phase is washed with water
  6. dry with materialdried with Na2SO4
  7. customre-evaporated
  8. customThe product is purified by column chromatography over silica gel 60 (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-c00a4e0454c94938b820681cf45f2404
Source dataset
uspto-grants-1996_08
Patent number
US05550129

Reaction notes

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