2-Naphthalenethiol → (E)-4-(2-naphthylthio)-3-buten-2-one
Reaction equation
CO/[CH:3]=[CH:4]/[C:5](=[O:7])[CH3:6].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[SH:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[S:18]/[CH:3]=[CH:4]/[C:5](=[O:7])[CH3:6]Participants
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (E)-4-methoxy-3-buten-2-one (purity: 90%, 15.0 ml, 0.13 mol) and 2-naphthalenethiol (21.16 g, 0.13 mol) in benzene (180 ml) was added p-toluene sulfonic acid-monohydrate (75 mg, 0.4 mmol), followed by heating, while stirring, on an oil bath at 50° C. for 70 minutes. After ice cooling, an aqueous saturated sodium hydrogen carbonate solution was added thereto, followed by extracting with ethyl acetate four times. The ethyl acetate layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine twice and then dried with anhydrous magnesium sulfate. After concentrating under a reduced pressure, the residue was treated with the column chromatography (670 g, n-hexane:methylene chloride:ethyl acetate=1:0:0-1:3:0-2:0:1), followed by recrystallizing from n-hexane-ethyl ether to thereby obtain the titled compound as a light brown crystalline.
Workup
- temperatureby heating
- extractionby extracting with ethyl acetate four times
- washThe ethyl acetate layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine twice
- dry with materialdried with anhydrous magnesium sulfate
- concentrationAfter concentrating under a reduced pressure
- additionthe residue was treated with the column chromatography (670 g, n-hexane:methylene chloride:ethyl acetate=1:0:0-1:3:0-2:0:1)
- customby recrystallizing from n-hexane-ethyl ether
Sources & evidence
- ORD record
- ord-8599bc832e8d4e51a44a3bf25ff4a4d8
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06049009
Reaction notes
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