Methyl propiolate → HCID 86743958, compound

HRID 1651365Notes

Reaction equation

HRID 1651365 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].C([Li])CCC.[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:17]([CH:18]=[CH:19][CH:20]=[O:21])=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[OH:21][CH:20](/[CH:19]=[CH:18]/[C:17]1[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:23][CH:22]=1)[C:3]#[C:2][C:1]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 13536Methyl propiolateHCID 25517Ammonium ChlorideHCID 2309953-(4-Methoxyphenyl)prop-2-enalHCID 178418339Butyllithium

Product 1

HCID 86743958HCID 86743958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5 ml (60 mmol) of methyl propiolate in 100 ml of tetrahydrofuran was treated at -78° under argon with 41.3 ml of n-butyllithium solution (1.6M in hexane). The mixture was stirred at -78° for 10 minutes and then a solution of 9.73 g (60 mmol) of 4-methoxycinnamaldehyde in 100 ml of tetrahydrofuran was added. The reaction mixture was stirred at -78° for 20 minutes, then warmed to -20° and treated with 100 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ether. The combined organic phases were washed with water, dried over sodium sulphate and concentrated. Flash chromatography of the residue on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1) yielded methyl (E)-4-hydroxy-6-(4-methoxyphenyl)-5-hexen-2-ynoate as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at -78° for 20 minutes
  2. temperaturewarmed to -20°
  3. extractionThe aqueous phase was extracted twice with ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71d4a7232fb5427a9d01a8dd0a432213
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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