Allyl Alcohol → HCID 22645478, compound

HRID 2414386Notes

Reaction equation

HRID 2414386 reaction equation
[N:1]1[C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:10](Cl)=[O:11].[CH2:13]([OH:16])[CH:14]=[CH2:15].CN1CC[O:21]CC1.[CH2:24]1[CH2:28]OC[CH2:25]1>CCOCC>[N:1]1[C:6]([C:7]([O:16][CH2:13][CH:14]=[CH2:15])=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:10]([O:11][CH2:28][CH:24]=[CH2:25])=[O:21]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 773352,6-Pyridinedicarbonyl dichloride

Product 1

HCID 22645478HCID 22645478, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

A stirred solution of 2,6-pyridinedicarboxylic acid chloride (3.51 g, 0.0172 mol) in 100 mL of THF is cooled to 0° C. then 12 mL (0.172 mol) of allyl alcohol and 7.1 mL (0.069 mol) of NMM are added simultaneously. The reaction is allowed to stir at 25° C. for 2 h, and then diluted with 100 mL of Et2O and washed with 100 mL water. The aqueous phase is extracted with Et2O (2×50 mL) and the combined extracts are washed with brine and dried with MgSO4. Filtration and concentration yields diallyl 2,6-pyridinedicarboxylate as a clear oil which is used without further purificiation.

Workup

  1. washwashed with 100 mL water
  2. extractionThe aqueous phase is extracted with Et2O (2×50 mL)
  3. washthe combined extracts are washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-87bf513575474935bff52d82d9592bb8
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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