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

HRID 1650250
Notes
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Reaction equation

HRID 1650250 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>[C:37]([C:34]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][CH:29]([OH:31])[CH2:30][S:13][CH2:12][CH:10]2[CH2:9][S:8][C:7]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])[S:11]2)=[C:25]([CH2:22][CH2:23][CH3:24])[C:35]=1[OH:36])(=[O:39])[CH3:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6569
Methyl Ethyl Ketone
Solvent

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-d63b11a7eff6458a93dfae48669189c8
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04923891

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes