1,3-Dibromopropane → ethyl 3,4-dihydro-2H-pyrano[2,3-b]indolizine-10-carboxylate

HRID 1939252Notes

Reaction equation

HRID 1939252 reaction equation
[Br-].[CH2:2]([O:4][C:5]([CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=O)[CH3:3].Br[CH2:21]CCBr.[OH-].[K+]>C(O)C.O>[O:4]1[C:5]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]3[N:8]([C:7]=2[CH2:21][CH2:3][CH2:2]1)[CH:13]=[CH:12][CH:11]=[CH:10]3

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 214672521,2-Di-[(ethoxycarbonyl)methyl]pyridinium bromide

Product 1

HCID 21467249ethyl 3,4-dihydro-2H-pyrano[2,3-b]indolizine-10-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 1,2-di-[(ethoxycarbonyl)methyl]pyridinium bromide (1.5 g, 0.0045 mole) and 1,3-dibromopropane (0.45 ml, 0.0045 mole) in ethanol (10 ml) was added over 5 minutes to a stirred solution of potassium hydroxide (0.75 g, 0.0134 mole) in ethanol (15 ml) at 5° C. The mixture was then allowed to warm upto room temperature and stir for 20 h. The reaction mixture was diluted with water (150 ml) and extracted with ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to leave a brown oil. This was chromatographed on silica gel eluting with ether to afford the title compound as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto leave a brown oil
  5. customThis was chromatographed on silica gel eluting with ether

Sources & evidence

ORD record
ord-e9e59f44f0d042cb8141c696d02a6c4e
Source dataset
uspto-grants-1997_12
Patent number
US05696129

Reaction notes

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