Sodium hydride → HCID 23332069, compound

HRID 1706409Notes

Reaction equation

HRID 1706409 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:17][C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>O1CCCC1.CN(C)C=O>[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][C:4]([S:7][CH2:17][C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 66144Ethyl bromopyruvateHCID 27604144-Phenylbenzene-1-thiol

Product 1

HCID 23332069HCID 23332069, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-biphenylthiol (2.79 g, 0.015 mole) in dry tetrahydrofuran (30 ml) and dimethylformamide (6 ml) was added portionwise sodium hydride (0.37 g, 0.015 mole) with stirring under a nitrogen atmosphere. The resulting solution was added dropwise over 45 min. to ethyl bromopyruvate (3.0 g, 0.015 mole) in dry tetrahydrofuran (30 ml) with stirring under nitrogen at -7° to -10° C. After 1 hr. at 25° C. ice-water (250 ml) was added. Extraction with methylene chloride (3×50 ml) followed by evaporation of the extract, and recrystallization of the residue from carbon tetrachloride gave 1.56 g (35%) of ethyl 3-(4-biphenylylthio)-2-oxopropionate, m.p. 154.5°-156° C.

Workup

  1. stirringwith stirring under nitrogen at -7° to -10° C
  2. extractionExtraction with methylene chloride (3×50 ml)
  3. customfollowed by evaporation of the extract, and recrystallization of the residue from carbon tetrachloride

Sources & evidence

ORD record
ord-8a7c333556f249d3a8ce86efaec4240a
Source dataset
uspto-grants-1980_06
Patent number
US04207329

Reaction notes

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