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

HRID 1383156Notes

Reaction equation

HRID 1383156 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][CH:29]1[O:31][CH2:30]1)[CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[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][S:13][CH2:30][CH:29]([OH:31])[CH2:28][O:27][C:26]2[CH:32]=[CH:33][C:34]([C:37](=[O:39])[CH3:38])=[C:35]([OH:36])[C:25]=2[CH2:22][CH2:23][CH3:24])[CH2:9][S:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27752301-(2-Hydroxy-4-(2-oxiranylmethoxy)-3-propylphenyl)ethanoneHCID 14405949Diethyl-4-(mercaptomethyl)-1,3-dithiolane-2,2-dipropanoate

Product 1

HCID 14405925Diethyl 4-[[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropyl]thio]methyl]-1,3-dithiolane-2,2-dipropanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The title compound was prepared according to the procedure of Example 2 using the mercaptan produced in Example 31 (1.5 g, 0.004 mol), 3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1,2-epoxypropane (described in U.S. Pat. No. 4,565,882) (1.1 g, 0.004 mol) and anhydrous potassium carbonate (1.75 g) in methyl ethyl ketone (15 ml). The crude product was chromatographed on silica gel using 30% ethyl acetate/hexane as eluent to give 1.9 g (60%) of the product as an oil.

Workup

  1. customThe crude product was chromatographed on silica gel using 30% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-40d5bf639fb44862b4996fd306e806ec
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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