Water → HCID 131715853, compound

HRID 893371Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=2)[S:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19](OC)=[O:20].[H-].[Na+].O>CN(C=O)C>[OH:20][CH:19]=[C:11]([S:10][C:9]1[CH:16]=[CH:17][CH:18]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

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-b2d0ddda7e61437a93de49e387046d8a
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05124353

Reaction notes

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