Acetic Acid → HCID 49849022, compound

HRID 1404444Notes

Reaction equation

HRID 1404444 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].[Li].[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH:16]1[O:20][C:19](=[O:21])[CH2:18][CH2:17]1.C(Br)CC.C(O)(=O)C>C1COCC1>[CH2:2]([CH:18]1[CH2:17][CH:16]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=2)[O:20][C:19]1=[O:21])[CH2:1][CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78401-BromopropaneHCID 45051747Lithium diisopropylamineHCID 67288682HCID 67288682, compound

Product 1

HCID 49849022HCID 49849022, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 2 M lithium diisopropylamine solution in THF of −78° C. is added 5-(pyridin-2-yl-methyl)dihydrofuran-2(3H)-one and the mixture is stirred for 1.5 hours at −78° C. Then 1-propyl bromide is added and the reaction is stirred for another 1.5 hours at −78° C. The reaction mixture is allowed to warm up to 0° C. before ice-cold water with acetic acid is added and subsequently extracted with 3 times dichloromethane. The dichloromethane is concentrated in vacuo and the residue is dissolved in dichloromethane, washed with saturated NaHCO3 and brine. Crude 3-propyl-5-(pyridin-2-ylmethyl)dihydrofuran-2(3H)-one is obtained after removal of the solvents in vacuo. The product is purified by column chromatography.

Workup

  1. stirringthe reaction is stirred for another 1.5 hours at −78° C
  2. additionis added
  3. extractionsubsequently extracted with 3 times dichloromethane
  4. concentrationThe dichloromethane is concentrated in vacuo
  5. dissolutionthe residue is dissolved in dichloromethane
  6. washwashed with saturated NaHCO3 and brine

Sources & evidence

ORD record
ord-c5ccb8fe74904aafb491a93ebad2a622
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

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