Potassium Carbonate → Diethyl 4-[[[4-(2-propylphenoxy)butyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoat

HRID 1383146Notes

Reaction equation

HRID 1383146 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.Br[CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][CH2:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>>[CH2:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[O:27][CH2:26][CH2:25][CH2:24][CH2:23][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)[CH2:35][CH3:36]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoateHCID 144059481-(4-Bromobutoxy)-2-propylbenzene

Product 1

HCID 14405903Diethyl 4-[[[4-(2-propylphenoxy)butyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoat

Procedure

The title compound was prepared according to the procedure of Example 2 using the mercaptan produced in Example 1 (2.0 g, 0.006 mol), the bromide produced in Example 22 (1.63 g, 0.006 mol) and anhydrous potassium carbonate (2.5 g). The crude product was chromatographed on silica gel using 15% ethyl acetate/hexane as eluent to give 2.78 g (87%) of the product as an oil.

Workup

  1. customThe crude product was chromatographed on silica gel using 15% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-937445b36b1f475fb58080313b1bb474
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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