Acetone → HCID 57772123, compound

HRID 1882306Notes

Reaction equation

HRID 1882306 reaction equation
[CH:1]1[C:5]2=[C:6](O)[C:7]3[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=3[CH:9]=[C:4]2[O:3][CH:2]=1.[C:16]([O-])([O-])=[O:17].[K+].[K+].[I-].[Na+].P(O)([O-])([O-])=[O:25].[Na+].[Na+].[CH3:31][C:32]([CH3:34])=[O:33]>>[CH3:16][O:17][C:31](=[O:25])[CH:32]([O:33][C:6]1[C:5]2[CH:1]=[CH:2][O:3][C:4]=2[CH:9]=[C:8]2[C:7]=1[CH:14]=[CH:13][C:11](=[O:12])[O:10]2)[CH3:34]

Participants

6

Reactant 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 5280371Bergaptol

Product 1

HCID 57772123HCID 57772123, compoundYield 38.5%

Procedure

To a mixture of Bergaptol (10 grams, 49.5 mmol), anhydrous K2CO3 (20 grams, 144.7 mmol), Sodium iodide (2.4 grams, 16 mmol), disodium phosphate (2.4 grams, 17 mmol) in anhydrous acetone (250 mL) was added methyl 2-chloro propionate (10 mL, 87.7 mmol) and refluxed for 8 hours. Acetone was distilled and water (100 mL) was added. Crude 40 was filtered and recrystallized in a mixture of methanol:chloroform (9:1) to give pure 40 (5.5 grams, 38.5%) as a white powder. The melting point was found to be 149.6-151.6° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 1.78 (d, 3H, —CH3), 3.68 (s, 3H, ester), 5.18 (q, 1H, CH), 6.31 (d, 1H, J=12.1 Hz, pyran), 6.84 (d, 1H, J=1.1 Hz, furan), 7.22 (s, 1H, Ar), 7.64 (d, 1H, J=1.1 Hz, furan), 8.36 (d, 1H, J=12.1 Hz, pyran).

Workup

  1. temperaturerefluxed for 8 hours
  2. distillationAcetone was distilled
  3. additionwater (100 mL) was added
  4. filtrationCrude 40 was filtered
  5. customrecrystallized in a mixture of methanol:chloroform (9:1)

Sources & evidence

ORD record
ord-137a39b9d12e4be4a1074ce384ea617b
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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