Potassium Carbonate → HCID 68618608, compound

HRID 1158453Notes

Reaction equation

HRID 1158453 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2].Br[CH2:18][CH2:19][CH2:20][O:21][CH3:22].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH2:18][CH2:19][CH2:20][O:21][CH3:22])[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 53689643HCID 53689643, compound

Product 1

HCID 68618608HCID 68618608, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 8-hydroxy-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid ethyl ester (1.65 g, 7.36 mmol), 1-bromo-3-methoxypropane (1.38 g, 8.83 mmol) and anhydrous K2CO3 (1.53 g, 11.0 mmol) in acetone (40 mL) is refluxed overnight. After cooling to room temperature, the mixture is poured into ice water and extracted with AcOEt. The organic layer is washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 3:1) yields the title compound as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.32. MS: 297.0 [M+H]+. 1H-NMR (CDCl3): δ 1.41 (t, 3H), 2.16 (m, 2H), 3.40 (s, 3H), 3.61 (m, 2H), 4.20 (m, 2H), 4.31 (m, 2H), 4.35-4.45 (m, 4H), 7.27 (d, 1H), 7.31 (d, 1H) ppm.

Workup

  1. temperatureis refluxed overnight
  2. extractionextracted with AcOEt
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (hexane/AcOEt 3:1)

Sources & evidence

ORD record
ord-98410e40aa294f668deb90039e9ec912
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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