Sodium borohydride → HCID 117992744, compound

HRID 922575Notes

Reaction equation

HRID 922575 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[CH2:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117993661HCID 117993661, compound

Product 1

HCID 117992744HCID 117992744, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude ethyl 2-(6-chloro-2-methoxypyridin-3-yl)acrylate (203 g, 0.84 mol) in MeOH (2 L) was added NaBH4 (63.8 g, 1.68 mol) in portions at 0° C. After addition, the reaction mixture was allowed to warm to r.t. over 2 h. The reaction solvent was removed under reduced pressure. The residue was treated with water and extracted with EtOAc twice. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (Petroleum ether→Petroleum ether:EtOAc=10:1) to afford ethyl 2-(6-chloro-2-methoxypyridin-3-yl)propanoate (126.5 g 62%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.21 (t, 3H), 1.44 (d, 3H), 3.88 (q, 1H), 3.95 (s, 3H), 4.13 (q, 2H), 6.89 (d, 1H), 7.46 (d, 1H).

Workup

  1. additionAfter addition
  2. customThe reaction solvent was removed under reduced pressure
  3. additionThe residue was treated with water
  4. extractionextracted with EtOAc twice
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel column chromatography (Petroleum ether→Petroleum ether:EtOAc=10:1)

Sources & evidence

ORD record
ord-0af10a0cd8f44ad98d8ed24c4f24a336
Source dataset
uspto-grants-2016_03
Patent number
US09278953B2

Reaction notes

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