Potassium Carbonate → Diethyl 4-[[[3 (4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]methyl]-1,3 oxathiolane-2,2-dipropanoate

HRID 1383133Notes

Reaction equation

HRID 1383133 reaction equation
[CH2:1]([C:4]1[C:14]([OH:15])=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH2:8][CH2:9]Br)[CH2:2][CH3:3].[SH:19][CH2:20][CH:21]1[CH2:25][O:24][C:23]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[S:22]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:16]([C:13]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][S:19][CH2:20][CH:21]2[CH2:25][O:24][C:23]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[S:22]2)=[C:4]([CH2:1][CH2:2][CH3:3])[C:14]=1[OH:15])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoate

Product 1

HCID 14405887Diethyl 4-[[[3 (4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]methyl]-1,3 oxathiolane-2,2-dipropanoateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(2-n-Propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane (2.0 g, 0.006 mol), prepared by the method described in U.S. Pat. No. 4,565,882, Example 14, incorporated herein by reference, was dissolved in methyl ethyl ketone (20 ml). To this solution was added the thiol of Example 1 (2.0 g, 0.006 mol) and anhydrous potassium carbonate (2.5 g) and the reaction mixture was refluxed with stirring under a nitrogen atmosphere for 24 hrs. The reaction was cooled to room temperature, filtered and the filtrate concentrated on the rotary evaporator. The residue was chromatographed on silica gel using 25% ethyl acetate/hexane as eluent to give 3.3 g (95%) of the title compound as an oil.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated on the rotary evaporator
  4. customThe residue was chromatographed on silica gel using 25% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-15e0897c7a0e4c90a9db0e79fe4d871b
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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