Propargyl bromide → HCID 53674013, compound

HRID 2073706Notes

Reaction equation

HRID 2073706 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:9]=[CH:10][C:11]([OH:13])=[O:12].[H][H].[CH2:16](Br)[C:17]#[CH:18]>CN(C=O)C>[CH3:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:9]=[CH:10][C:11]([O:13][CH2:18][C:17]#[CH:16])=[O:12]

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 156896HCID 156896, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53674013HCID 53674013, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

At 10° C., 0.9 g of sodium hydride was added to a solution of 6.2 g of 3-(3-methylthiophen-2-yl)-propenoic acid in 100 ml of absolute DMF. When no more hydrogen evolved, 4.9 g of propargyl bromide was dripped in at room temperature and the mixture was then heated at 50° C. for 3 hours. The reaction mixture was poured onto icewater, the aqueous phase was extracted three times with ethyl acetate, and the combined organic extracts were dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was recrystallized from ethanol. There was obtained 3.9 g of propargyl 3-(3-methylthiophen-2-yl)-propenoate of melting point 84' to 86° C.

Workup

  1. customwas dripped in at room temperature
  2. additionThe reaction mixture was poured onto icewater
  3. extractionthe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. customAfter removal of the solvent under reduced pressure
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-20dea7e2b9504e5a9a7c589bd5b1d35c
Source dataset
uspto-grants-1990_04
Patent number
US04920110

Reaction notes

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