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

HRID 1383150Notes

Reaction equation

HRID 1383150 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]1([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[S:11][CH:10]([CH2:12][SH:13])[CH2:9][S:8]1)[CH3:2].[CH2:22]([C:25]1[C:35]([OH:36])=[C:34]([C:37](=[O:39])[CH3:38])[CH:33]=[CH:32][C:26]=1[O:27][CH2:28][CH2:29][CH2:30]Br)[CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:37]([C:34]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][CH2:29][CH2:30][S:13][CH2:12][CH:10]2[CH2:9][S:8][C:7]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])[S:11]2)=[C:25]([CH2:22][CH2:23][CH3:24])[C:35]=1[OH:36])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 14405949Diethyl-4-(mercaptomethyl)-1,3-dithiolane-2,2-dipropanoate

Product 1

HCID 14405911Diethyl 4-[[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]methyl]-1,3-dithiolane-2,2-dipropanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The title compound was prepared by the procedure of Example 2 using the mercaptan produced in Example 31 (2.0 g, 0.0056 mol), 3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane (prepared as described in U.S. Pat. No. 4,565,882, Example 14) (2.0 g, 0.006 mol) and anhydrous potassium carbonate (3.5 g) in methyl ethyl ketone (25 ml) at reflux overnight. The crude product was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent to give 2.1 g (70%) of the product as an oil.

Workup

  1. customprepared
  2. customThe crude product was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-0dad4dee63ed431e852773a226a0679c
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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