Water → HCID 131715853, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1.[CH:19](OC)=[O:20].[H-].[Na+].O>CN(C=O)C>[OH:20][CH:19]=[C:4]([S:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1)[C:3]([O:2][CH3:1])=[O:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl(3-phenylthiophenoxy)acetate (6.60 g) and methyl formate (30.78 g) were dissolved in DMF (30 ml) and added dropwise at 0° C. to sodium hydride (0.83 g, 50% dispersion in oil) in DMF. The reaction mixture was stirred at 0° C. for 45 minutes and then left at room temperature under nitrogen over the weekend. The reaction mixture was then poured into water (300 ml) and washed with diethyl ether (3×150 ml). The aqueous phase was adjusted to pH 7 with hydrochloric acid and then extracted with diethyl ether (3×100 ml). The combined organic extracts were washed successively with water (3×100 ml) and brine (2×75 ml) and then dried. Filtration and evaporation of the solvent under reduced pressure gave methyl 3-hydroxy-2-(3'-phenylthiophenoxy)propenoate (1.13 g) which was used without further purification.
Workup
- waitleft at room temperature under nitrogen over the weekend
- washwashed with diethyl ether (3×150 ml)
- extractionextracted with diethyl ether (3×100 ml)
- washThe combined organic extracts were washed successively with water (3×100 ml) and brine (2×75 ml)
- customdried
- filtrationFiltration and evaporation of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-b0242d8160af41c5bf7fbf5d0ab5b62f
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04802913
Reaction notes
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