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

HRID 539276

반응식

HRID 539276 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 (2M) 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, 3 H), 4.87 (q, 2 H), 7.57 (dd, 1H), 8.14 (d, 1 H), 8.34 (d, 1 H); 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-1263363c02444c5194eebebd26b84ae4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865911B2

연결된 노트

불러오는 중…