Diethyl Ether → HCID 53745626, compound

HRID 2073707Notes

Reaction equation

HRID 2073707 reaction equation
[CH2:1](O)[C:2]#[CH:3].[Cl:5][C:6]1[S:7][CH:8]=[C:9]([CH:12]=[CH:13][C:14](Cl)=[O:15])[C:10]=1[Cl:11].C([O:19]CC)C>N1C=CC=CC=1>[Cl:5][C:6]1[S:7][CH:8]=[C:9]([CH:12]=[CH:13][C:14]([O:15][CH2:3][C:2]#[CH:1])=[O:19])[C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7859Propargyl alcoholHCID 54405814HCID 54405814, compound

Product 1

HCID 53745626HCID 53745626, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.7 g of propargyl alcohol was dissolved in 50 ml of absolute pyridine. At 0° C. at most, 18.4 g of 3-(2,3-dichlorothiophen-4-yl)-propenoyl chloride was added and the reaction batch was stirred for 12 hours at room temperature. 50 ml of diethyl ether was added, the precipitated pyridine hydrochloride was filtered off and the filtrate concentrated under reduced pressure. The residue was taken up in 150 ml of ethyl acetate, the mixture was shaken with water and the organic phase was dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was recrystallized from methanol. There was obtained 7.6 g of propargyl 3-(2,3-dichlorothiophen-4-yl)-propenoate of melting point 84° to 86° C.

Workup

  1. filtrationthe precipitated pyridine hydrochloride was filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. stirringthe mixture was shaken with water
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customAfter removal of the solvent under reduced pressure
  6. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-7c49ee5647bc44ab8f12267ec7c44b5c
Source dataset
uspto-grants-1990_04
Patent number
US04920110

Reaction notes

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