Acetone → HCID 19762688, compound

HRID 1461164Notes

Reaction equation

HRID 1461164 reaction equation
[C:1]([C:4]1[CH:32]=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]3[CH2:17][CH2:18][CH:19]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[O:20][C:15]=3[C:14]=2[CH2:28][CH2:29][CH3:30])=[C:6]([CH2:33][CH2:34][CH3:35])[C:5]=1O)(=[O:3])[CH3:2].[CH3:37]C(C)=O.S([O:46][CH3:47])(OC)(=O)=O>[OH-].[K+]>[C:1]([C:4]1[CH:32]=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]3[CH2:17][CH2:18][CH:19]([CH2:21][CH2:22][C:23]([O:25][CH3:37])=[O:24])[O:20][C:15]=3[C:14]=2[CH2:28][CH2:29][CH3:30])=[C:6]([CH2:33][CH2:34][CH3:35])[C:5]=1[O:46][CH3:47])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 1469513-{7-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propoxy]-8-propyl-3,4-dihydro-2H-1-benzopyran-2-yl}propanoic acid

Product 1

HCID 19762688HCID 19762688, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

7-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-propionic acid (1 mmol) is dissolved in acetone containing 2.5 equivalents of potassium hydroxide and 3 equivalents of dimethyl sulfate. The mixture is heated at 40° C. for about 10 hours then cooled. The solvent is removed in vacuo, and the residue is partitioned between ethyl acetate and water. The organic layer is separated and dried over magnesium sulfate. Removal of the volatiles in vacuo gives the product.

Workup

  1. temperaturethen cooled
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between ethyl acetate and water
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the volatiles in vacuo
  7. customgives the product

Sources & evidence

ORD record
ord-6aa38fa1a9cd4b1cb202fd3a4803154b
Source dataset
uspto-grants-1991_12
Patent number
US05073562

Reaction notes

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