Potassium Carbonate → Diethyl 4-[[(3-phenoxypropyl)thio]methyl]-1,3-oxathiolane-2,2-dipropanoate

HRID 1383137Notes

Reaction equation

HRID 1383137 reaction equation
[SH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:4]1.[O:22]([CH2:29][CH2:30][CH2:31]Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[O:22]([CH2:29][CH2:30][CH2:31][S:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:4]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoate

Product 1

HCID 14405891Diethyl 4-[[(3-phenoxypropyl)thio]methyl]-1,3-oxathiolane-2,2-dipropanoateYield 96%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The product of Example 1 (2.0 g, 0.006 mol) and 3-phenoxy-1-bromopropane (1.3 g, 0.006 mol) were dissolved in methyl ethyl ketone (20 ml). Anhydrous potassium carbonate (2.5 g) was added and the reaction was run and worked up as described in the procedure of Example 2. Chromotography of the resulting oil on silica gel using 15% ethyl acetate/hexane as eluent gave 2.70 g (96%) of the title compound as an oil.

Sources & evidence

ORD record
ord-9a04a0a7e58d49c1a2831debf2a189e9
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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