Allyl Alcohol → HCID 22645497, compound

HRID 2414387Notes

Reaction equation

HRID 2414387 reaction equation
[N:1]1[C:6]([C:7](OCC=C)=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14].C(O)C=C.[BH4-].[Na+].C(OCC)C.CCCCCC>C1COCC1>[OH:8][CH2:7][C:6]1[N:1]=[C:2]([C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH:3]=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 4311764Sodium borohydrideHCID 21584099Diethylether hexaneHCID 22645478HCID 22645478, compound

Product 1

HCID 22645497HCID 22645497, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of diallyl 2,6-pyridinedicarboxylate (17.1 g, 0.069 mol) in 150 mL of THF, and 150 mL of allyl alcohol is stirred at room temperature. Sodium borohydride (1.32 g, 0.035 mol) is added in several portions over 10 minutes, and the reaction is allowed to stir at room temperature for 15 h. The reaction is quenched by slow addition of 30 mL of water, followed by 30 mL of 1.0 N HCl. The mixture is poured into a separatory funnel containing 100 mL of 5% ammonium hydroxide and extracted with 1:1 ethyl acetate-diethyl ether (3×100 mL). The combined organic fractions are washed with brine, dried with MgSO4, filtered, and concentrated in vacuo to give a yellow oil which solidified on standing. Trituration with 1:1 diethyl ether/hexane affords allyl 6-(hydroxymethyl)pyridine-2-carboxylate as a white crystalline solid.

Workup

  1. stirringto stir at room temperature for 15 h
  2. customThe reaction is quenched by slow addition of 30 mL of water
  3. additionThe mixture is poured into a separatory funnel
  4. additioncontaining 100 mL of 5% ammonium hydroxide
  5. extractionextracted with 1:1 ethyl acetate-diethyl ether (3×100 mL)
  6. washThe combined organic fractions are washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a yellow oil which

Sources & evidence

ORD record
ord-6c2df25fcb2c4e89868ed28226663983
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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