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Potassium Carbonate → Ethyl 3-[[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropyl]thio]methyl]-1-oxa-4-thiaspiro[4.4]nonane-7-acetate

HRID 1608278
Notes
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Reaction equation

HRID 1608278 reaction equation
[CH2:1]([C:4]1[C:14]([OH:15])=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH:8]1[O:10][CH2:9]1)[CH2:2][CH3:3].[SH:19][CH2:20][CH:21]1[CH2:25]S[C:23]2([CH2:29][CH2:28][CH:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:26]2)[S:22]1.C(=O)([O-])[O-:37].[K+].[K+]>C(C(C)=O)C>[C:16]([C:13]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH:8]([OH:10])[CH2:9][S:19][CH2:20][CH:21]2[S:22][C:23]3([CH2:29][CH2:28][CH:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:26]3)[O:37][CH2:25]2)=[C:4]([CH2:1][CH2:2][CH3:3])[C:14]=1[OH:15])(=[O:18])[CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27752301-(2-Hydroxy-4-(2-oxiranylmethoxy)-3-propylphenyl)ethanoneHCID 19849025Ethyl 2-(mercaptomethyl)-1,4-dithiaspiro[4.4]nonane-7-acetate

Product 1

HCID 19849026Ethyl 3-[[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropyl]thio]methyl]-1-oxa-4-thiaspiro[4.4]nonane-7-acetate

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Procedure

3-(2-n-Propyl-3-hydroxy-4-acetylphenoxy)-1,2-epoxypropane (1.5 g, 0.006 mol) (described in U.S. Pat. No. 4,565,882) is dissolved in 20 ml of methyl ethyl ketone. To this solution is added the mercaptan of Example G (1.75 g, 0.006 mol) and anhydrous potassium carbonate (2.5 g) and the reaction mixture is refluxed with stirring under a nitrogen atmosphere for 24 hrs. The reaction is cooled to room temperature, filtered and the filtrate is concentrated on a rotary evaporator. The residue is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the titled compound.

Workup

  1. temperaturethe reaction mixture is refluxed
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated on a rotary evaporator
  4. customThe residue is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-2057bcd097f74eca890cf6d2e7e04cfe
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04870098

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes