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

HRID 1383153Notes

Reaction equation

HRID 1383153 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.[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:37]([C:34]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][CH:29]([OH:31])[CH2:30][S:1][CH2:2][CH:3]2[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]2)=[C:25]([CH2:22][CH2:23][CH3:24])[C:35]=1[OH:36])(=[O:39])[CH3:38]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27752301-(2-Hydroxy-4-(2-oxiranylmethoxy)-3-propylphenyl)ethanoneHCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoate

Product 1

HCID 14405915Diethyl 4-[[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoate

Procedure

The title compound was prepared according to the procedure of Example 2 using the mercaptan produced in Example 1 (2.0 g, 0.0066 mol), 3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1,2-epoxypropane (described in U.S. Pat. No. 4,565,882) (1.5 g, 0.006 mol) and anhydrous potassium carbonate (3.0 g). The crude product was chromatographed on silica gel using 40% ethyl acetate/hexane as eluent to give 3.22 g (92%) of the product as an oil.

Workup

  1. customThe crude product was chromatographed on silica gel using 40% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-9185ffb09d474a3189357097a0643484
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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