Delta-Valerolactone → HCID 14576266, compound

HRID 1492020Notes

Reaction equation

HRID 1492020 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[C:13]1(=[O:19])[O:18][CH2:17][CH2:16][CH2:15][CH2:14]1>CCCCCC.CCOCC>[OH:19][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:18]

Participants

6

Reactant 3

HCID 10953Delta-ValerolactoneHCID 122863-BromopyridineHCID 178418339Butyllithium

Product 1

HCID 14576266HCID 14576266, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution prepared by adding 497 ml (1 mole) of 2.01 molar solution of n-butyllithium in hexane into 2 l of ether at -60° C., is added dropwise with stirring under argon at -78° C. a solution of 172 g (1.09 mole) of 3-bromopyridine in 50 ml of ether over a period of 15 min. The mixture is stirred at -78° C. for an additional 30 min and a solution of 100 g(1 mole) of δ-valerolactone in 100 ml of ether is added dropwise over a period of 15 min. The mixture is stirred at -78° C. for 3 h, quenched with 500 ml of concentrated aqueous ammonium chloride, washed with water, dried (MgSO4) and evaporated to give 5-hydroxy-1-(3-pyridyl)pentan-1-one as an oil.

Workup

  1. customTo a solution prepared
  2. additionis added dropwise
  3. stirringThe mixture is stirred at -78° C. for 3 h
  4. customquenched with 500 ml of concentrated aqueous ammonium chloride
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-638c0d4253fe418d986b0f5ea4fe40c0
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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