2-Propynoic acid, 3-phenyl-, ethyl ester → HCID 23047420, compound

HRID 2107081Notes

Reaction equation

HRID 2107081 reaction equation
[C:1]1([C:7]#[C:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.NC1O[C:22]([CH:33]([CH3:35])[CH3:34])=[N+:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=12>C(#N)C>[CH:33]([C:22]1[N:23]2[CH:32]=[CH:31][C:30]3[C:25]([C:24]2=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:26][CH:27]=[CH:28][CH:29]=3)([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 12472226HCID 12472226, compound

Product 1

HCID 23047420HCID 23047420, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl phenylpropiolate (10.1 g, 0.058 mol) was added with stirring to a solution of 1-amino-3-isopropyloxazolo[4,3-a]isoquinolinium tetrafluoroborate (9.1 g) in acetonitrile (90 ml) at 50° C. The solution was then heated at reflux for 30 minutes and it was then evaporated in vacuo to give a viscous orange-brown oil, which was extracted with hot petroleum ether (b.p. 60°-80° C.)(4×100 ml). The petroleum extract was evaporated in vacuo and the residue was subjected to flash chromatography on silica gel using as eluent a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v), giving an oil, which crystallised on standing, to give ethyl 3-isopropyl-1-phenylpyrrolo-[ 2,1-a]isoquinoline-2-carboxylate (1.7 g), in the form of a colourless solid, m.p. 82°-84° C. [N.M.R. (in CDCl3): 0.88 (3H, t, J=7 Hz), 1.52 (6H, d, J=7 Hz), 4.01 (2H, q, J=7 Hz), 4.14 (1H, septet, J=7 Hz), 6.75 (1H, d, J=8 Hz), 7.00-7.50 (9H, m), and 7.85 (1H, d, J=8 Hz)].

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 30 minutes
  3. customit was then evaporated in vacuo
  4. customto give a viscous orange-brown oil, which
  5. extractionwas extracted with hot petroleum ether (b.p. 60°-80° C.)(4×100 ml)
  6. extractionThe petroleum extract
  7. customwas evaporated in vacuo
  8. additiona mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v)
  9. customgiving an oil, which
  10. customcrystallised

Sources & evidence

ORD record
ord-7e780c835bc64279bef293d4da84130b
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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