Butyn-2-one → 10-acetyl-4,5-dihydro-8-(m-fluorophenyl)7H-thieno[2,3-a]quinolizin-7-one

HRID 1087530Notes

Reaction equation

HRID 1087530 reaction equation
[OH-].[OH:2][C:3]1[N+:7]2[CH2:8][CH2:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]=2S[C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1.[CH3:22][C:23](=[O:26])[C:24]#[CH:25]>C1(C)C=CC=CC=1>[C:23]([C:24]1[CH:25]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:3](=[O:2])[N:7]2[C:6]=1[C:11]1[S:12][CH:13]=[CH:14][C:10]=1[CH2:9][CH2:8]2)(=[O:26])[CH3:22]

Participants

4

Reactant 2

HCID 15018Butyn-2-oneHCID 14770024HCID 14770024, compound

Product 1

HCID 1902048310-acetyl-4,5-dihydro-8-(m-fluorophenyl)7H-thieno[2,3-a]quinolizin-7-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.303 g of 5,6-dihydro-3-hydroxy-2-(m-fluorophenyl)-thiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide (internal salt) and 0.145 ml of 3-butyn-2-one in 5 ml of toluene was heated under reflux for 1 hour. The solvent is evaporated in vacuo and the residue is chromatographed over silica gel with toluene/ethyl acetate (1:1). After recrystallization from ethanol, there was obtained 10-acetyl-4,5-dihydro-8-(m-fluorophenyl)-7H-thieno[2,3-a]quinolizin-7-one of m.p. 109°-110°.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is chromatographed over silica gel with toluene/ethyl acetate (1:1)
  4. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-cd03a6316b324feabac1ec7e63a654ea
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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