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

HRID 539276

反応式

HRID 539276 の反応式
[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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 58449213Methyl 5-(but-2-yn-1-yloxy)picolinate2 回

生成物 1

HCID 679795075-(But-2-ynyloxy)picolinic acid収率 45.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-1263363c02444c5194eebebd26b84ae4
出典データセット
uspto-grants-2014_10
特許番号
US08865911B2

関連ノート

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