Sodium borohydride → 4-(Hydroxymethyl)-6-methylpicolinonitrile

HRID 2071152

반응식

HRID 2071152 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:6](OC)=[O:7])#[N:2].[BH4-].[Na+]>CO.C1COCC1>[OH:7][CH2:6][C:5]1[CH:10]=[C:11]([CH3:13])[N:12]=[C:3]([C:1]#[N:2])[CH:4]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 58802283Methyl 2-cyano-6-methylisonicotinate

생성물 1

HCID 591848654-(Hydroxymethyl)-6-methylpicolinonitrile수율 40.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring solution of 1.3 g (7.33 mmol) of methyl 2-cyano-6-methylisonicotinate in 25 mL of MeOH and 5 mL of THF at 0° C. was added 823 mg (21.7 mmol) of NaBH4. After 2 h the ice bath was removed and stirring was continued with warming to r.t. and after a further 15 min. 1.06 g of NaBH4 was added. After another 15 min., the solution was concentrated, and EtOAc was added. The pH was adjusted to 7 with 1N HCl, and the layers were separated. The aqueous layer was extracted with EtOAc (2×), and the combined extracts were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (2-3) % MeOH/CHCl3 provided 440 mg of 4-(hydroxymethyl)-6-methylpicolinonitrile in 40% yield as a colorless solid.

후처리

  1. customAfter 2 h the ice bath was removed
  2. addition1.06 g of NaBH4 was added
  3. concentrationthe solution was concentrated
  4. additionEtOAc was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc (2×)
  7. washthe combined extracts were washed with brine (50 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash silica gel chromatography (2-3) % MeOH/CHCl3

출처 및 근거

ORD 기록
ord-7584de6511304bdc97e058180d6b5df6
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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