Dimethyl pyridine-2,6-carboxylate → Methyl 6-(hydroxymethyl)picolinate

HRID 1174196

반응식

HRID 1174196 반응식
[N:1]1[C:6]([C:7](OC)=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:11]([O:13][CH3:14])=[O:12].[BH4-].[Na+]>CO.O1CCCC1>[OH:8][CH2:7][C:6]1[N:1]=[C:2]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=[CH:4][CH:5]=1

참가 물질

5

반응물 2

HCID 79549Dimethyl pyridine-2,6-carboxylateHCID 4311764Sodium borohydride

생성물 1

HCID 11513809Methyl 6-(hydroxymethyl)picolinate수율 56%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of dimethyl 2,6-pyridine-dicarboxylate (100 g, 513 mmol) in methanol (800 mL) and tetrahydrofuran (300 mL) was heated to dissolve and while the solution was still hot, it was treated in portions with sodium borohydride (18.2 g, 479 mmol) over 1 hour. The mixture was stirred for 1 hour at room temperature, cooled to 0-5° C., and quenched with 10% citric acid (160 mL), stirred for another 15 minutes, and filtered. The filtrate was concentrated, dissolved in dichloromethane, dried (sodium sulfate), filtered, and concentrated to a white solid. The solid was heated to dissolve in ethyl acetate (100 mL), stirred for 16 hours at room temperature, filtered and concentrated to give the title compound (44.5 g, 56% yield). 1H NMR (CDCl3) δ ppm 3.50(s, 1H), 4.00 (s, 3 H), 4.86 (s, 2 H), 7.52 (d, 1 H), 7.85 (t, 1 H), 8.04 (d, 1 H).

후처리

  1. temperaturewas heated
  2. dissolutionto dissolve and while the solution
  3. temperaturecooled to 0-5° C.
  4. customquenched with 10% citric acid (160 mL)
  5. stirringstirred for another 15 minutes
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. dissolutiondissolved in dichloromethane
  9. dry with materialdried (sodium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated to a white solid
  12. temperatureThe solid was heated
  13. dissolutionto dissolve in ethyl acetate (100 mL)
  14. stirringstirred for 16 hours at room temperature
  15. filtrationfiltered
  16. concentrationconcentrated

출처 및 근거

ORD 기록
ord-18392a829c054434a7bfa1493843c477
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834043B2

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