Methyl Ethyl Ketone → Diethyl 4-[[[5 (2-propylphenoxy)pentyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoate

HRID 1383139Notes

Reaction equation

HRID 1383139 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[SH:20][CH2:21][CH:22]1[CH2:26][O:25][C:24]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[S:23]1.[CH2:41]([C:43](C)=O)[CH3:42]>>[CH2:42]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][S:20][CH2:21][CH:22]1[CH2:26][O:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[S:23]1)[CH2:41][CH3:43]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 140973Benzene, ((5-bromopentyl)oxy)-HCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoate

Product 1

HCID 14405892Diethyl 4-[[[5 (2-propylphenoxy)pentyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoateYield 80%

Procedure

Potassium carbonate (2.5 g) was mixed with a solution of 5-phenoxy-1-bromopentane (1.7 g, 0.006 mol) and the product of Example 1 (2.0 g, 0.006 mol) in methyl ethyl ketone (20 ml). The reaction mixture was stirred and refluxed under a nitrogen atmosphere for 4 hrs and then worked up according to the procedure described in Example 2. The residue was chromatographed on silica gel using 4% acetone/benzene as eluent to give 1.8 g (80%) of the title compound as an oil.

Workup

  1. temperaturerefluxed under a nitrogen atmosphere for 4 hrs
  2. customThe residue was chromatographed on silica gel using 4% acetone/benzene as eluent

Sources & evidence

ORD record
ord-8ce5e70fb53743c1a8f28ce4fb4f1197
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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