Methanol → HCID 14666697, compound

HRID 477922Notes

Reaction equation

HRID 477922 reaction equation
[O:1]=[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([C:18](O)=O)=[C:8]2[N:3]1[CH2:4][CH2:5][C:6]1[CH:23]=[CH:22][S:21][C:7]=12.B.CSC.CO>O1CCCC1>[CH3:18][C:9]1[CH:10]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2](=[O:1])[N:3]2[C:8]=1[C:7]1[S:21][CH:22]=[CH:23][C:6]=1[CH2:5][CH2:4]2

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 14666689HCID 14666689, compound

Product 1

HCID 14666697HCID 14666697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.646 g of 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylic acid was dissolved in 20 ml of tetrahydrofuran. The solution was treated at -15° with 0.4 ml of a 10M solution of borane/methyl sulfide in tetrahydrofuran, left to warm to room temperature and subsequently heated under reflux for 2 hours. After cooling to room temperature, the reaction mixture was treated with methanol and evaporated in vacuo. The mixture was heated to boiling in 2N hydrochloric acid for a short time and extracted with chloroform. The organic extracts was washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo. After recrystallization from ethyl acetate/diethyl ether there was obtained pure 4,5-dihydro-10-methyl-8-phenyl-7H-thieno-[2,3-a]quinolizin-7-one of m.p. 80.5°-81°.

Workup

  1. waitleft
  2. temperaturesubsequently heated
  3. temperatureunder reflux for 2 hours
  4. temperatureAfter cooling to room temperature
  5. customevaporated in vacuo
  6. temperatureThe mixture was heated
  7. extractionextracted with chloroform
  8. washThe organic extracts was washed with saturated aqueous sodium bicarbonate solution
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customAfter recrystallization from ethyl acetate/diethyl ether there

Sources & evidence

ORD record
ord-9186b62b8252474b8d9248ea179a2b0c
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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