Picolyl chloride → HCID 20432090, compound

HRID 2412667Notes

Reaction equation

HRID 2412667 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7]Cl.[Na].[OH:10][CH2:11][C:12]1([CH3:20])[O:16][C:15]([CH3:19])([C:17]#[N:18])[CH2:14][CH2:13]1>CN(C)C=O>[CH3:19][C:15]1([C:17]#[N:18])[CH2:14][CH2:13][C:12]([CH3:20])([CH2:11][O:10][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[O:16]1

Participants

5

Reactant 3

HCID 23393Picolyl chlorideHCID 5360545SodiumHCID 13309739HCID 13309739, compound

Product 1

HCID 20432090HCID 20432090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Freshly liberated 2-picolinyl chloride was secured by extracting a mixture of 1.48 g potassium carbonate and 1.64 g 2-picolinyl chloride in 10 ml water with methylene chloride. The extract was dried (MgSO4) and concentrated (rotary evaporator). To the residue was added 10 ml dry dimethylformamide and the remaining methylene chloride was removed by further evaporation. The resulting solution was then added to a mixture of 10 mmol of the sodium salt of tetrahydro-5-(hydroxymethyl)-2,5-dimethyl-2-furancarbonitrile as a mixture of cis-trans isomers in 10 ml dry dimethylformamide prepared as described in Embodiment 10 above. The reaction progress and workup also followed the procedure for Embodiment 10 with the exception that crude product was secured from both pentane and ether extraction of the ice-quenched mixture. The crude product, which consisted of both cis- and trans-isomers, was purified and isomerically separated by preparative hplc using a silica gel column and ethyl acetate:pentane (60:40) as eluent. The cis (Z)-isomer amounted to 0.69 g, bp not determined.

Workup

  1. extractionby extracting
  2. additiona mixture of 1.48 g potassium carbonate and 1.64 g 2-picolinyl chloride in 10 ml water with methylene chloride
  3. dry with materialThe extract was dried (MgSO4)
  4. concentrationconcentrated
  5. custom(rotary evaporator)
  6. additionTo the residue was added 10 ml dry dimethylformamide
  7. customthe remaining methylene chloride was removed by further evaporation
  8. customprepared
  9. extractionwas secured from both pentane and ether extraction of the ice-
  10. customquenched mixture
  11. customwas purified
  12. customisomerically separated by preparative hplc

Sources & evidence

ORD record
ord-1e241f415f0046a7b30cb3d0fc1ed60c
Source dataset
uspto-grants-1985_01
Patent number
US04493936

Reaction notes

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