Sodium hydride → Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate

HRID 1741825Notes

Reaction equation

HRID 1741825 reaction equation
[H-].[Na+].C([O:6][C:7]1[CH:31]=[CH:30][C:10]([C:11]([C:13]2[CH:14]=[C:15]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:16]3[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]3)=[O:12])=[CH:9][CH:8]=1)(=O)C>C(O)C.O1CCCC1>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([C:13]2[CH:14]=[C:15]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:16]3[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]3)=[O:12])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 10862141HCID 10862141, compound

Product 1

HCID 11824313Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrateYield 90.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil) (4.38 g) was added to an ice cold solution of ethyl 4-[1-(4-acetoxybenzoyl)indolizin-3-yl]butyrate (36.1 g) in a mixture of ethanol (200 ml) and tetrahydrofuran (200 ml). The mixture was stirred for 20 minutes at 0° C. and evaporated. The residual solution was poured into a mixture of diluted hydrochloric acid and ice, and extracted with a mixture of chloroform and methanol (10:1). The organic layer was washed with a sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and evaporated. The residue was washed with ethyl acetate and diethyl ether to give ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate as yellow powder (29.3 g).

Workup

  1. customevaporated
  2. additionThe residual solution was poured into a mixture of diluted hydrochloric acid and ice
  3. extractionextracted with a mixture of chloroform and methanol (10:1)
  4. washThe organic layer was washed with a sodium bicarbonate aqueous solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. washThe residue was washed with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-a9433e74703b42c1ac742da00e6f6988
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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