Hydrochloric Acid → 5-(But-2-ynyloxy)picolinic acid

HRID 1770886

반응식

HRID 1770886 반응식
[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=[O:13])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4].[OH-].[Li+].CCOC(C)=O.Cl>C1COCC1.O>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 58449213Methyl 5-(but-2-yn-1-yloxy)picolinate2회

생성물 1

HCID 679795075-(But-2-ynyloxy)picolinic acid수율 45.4%

시약·촉매·용매 2

HCID 962Water용매3회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 5-(but-2-ynyloxy)picolinate (Intermediate 18, 1.42 g, 6.92 mmol) in THF (15 mL) was added lithium hydroxide (0.871 g, 20.76 mmol) dissolved in water (5 mL) to the reaction mixture at r.t. After 3 days of stirring was the reaction mixture partioned between water and EtOAc. The water was made acidic with aq. solution of HCl (2 M) and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated to give 0.60 g (45% yield) of the title compound: 1H NMR (500 MHz, CD3OD) δ ppm 1.84 (t, 3H), 4.87 (q, 2H), 7.57 (dd, 1H), 8.14 (d, 1H), 8.34 (d, 1H); MS (ES+) m/z 192 [M+H]+.

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a10967dd17714091a5ba33d639fc3db5
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09248129B2

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