Acetone → Methyl 7-[[5-(4-acetyl-3-methoxy-2-propylphenoxy)pentyl]oxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate

HRID 478024Notes

Reaction equation

HRID 478024 reaction equation
[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]3[CH2:19][CH2:20][CH:21]([C:23]([O:25][CH3:26])=[O:24])[O:22][C:17]=3[C:16]=2[CH2:29][CH2:30][CH3:31])=[C:6]([CH2:34][CH2:35][CH3:36])[C:5]=1[OH:37])(=[O:3])[CH3:2].[CH3:38]C(C)=O.S(OC)(OC)(=O)=O>[OH-].[K+]>[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]3[CH2:19][CH2:20][CH:21]([C:23]([O:25][CH3:26])=[O:24])[O:22][C:17]=3[C:16]=2[CH2:29][CH2:30][CH3:31])=[C:6]([CH2:34][CH2:35][CH3:36])[C:5]=1[O:37][CH3:38])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 135378702-Carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchroman

Product 1

HCID 14722866Methyl 7-[[5-(4-acetyl-3-methoxy-2-propylphenoxy)pentyl]oxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 7-[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]oxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate (1 mMol), prepared as described in U.S. Pat. No. 4,565,882, was dissolved in acetone containing 2.5 equivalents of potassium hydroxide and 3 equivalents of dimethyl sulfate. The mixture was heated at 40° C. for 10 hours and then cooled; the solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was separated and dried over magnesium sulfate. Evaporation of the volatiles in vacuo afforded the methyl ether.

Workup

  1. temperaturecooled
  2. customthe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the volatiles in vacuo

Sources & evidence

ORD record
ord-f81d366078034e35837fc799910c0f83
Source dataset
uspto-grants-1989_12
Patent number
US04889871

Reaction notes

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