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Potassium Hydroxide → 5-(Cyclopropylmethoxy)pyrazine-2-carboxylic acid

HRID 517044
ノート
印刷プレビュー

反応式

HRID 517044 の反応式
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH:11]1([CH2:14][OH:15])[CH2:13][CH2:12]1.[OH-].[K+]>CS(C)=O>[CH:11]1([CH2:14][O:15][C:2]2[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=2)[CH2:13][CH2:12]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 75644CyclopropanemethanolHCID 4654725-Chloropyrazinoic acid

生成物 1

HCID 574758755-(Cyclopropylmethoxy)pyrazine-2-carboxylic acid収率 34%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A solution of 5-chloro-pyrazine-2-carboxylic acid (1.50 g, 9.46 mmol) in dry dimethylsulfoxide (5 ml) was treated at 25° C. with cyclopropyl-methanol (1.02 g, 14.1 mmol) and powdered potassium hydroxide (2.12 g, 37.4 mmol). The mixture was heated in a microwave oven at 80° C. for 90 minutes. For the workup, the reaction mixture was quenched with an aqueous solution of citric acid (10%), then extracted with ethyl acetate (5×30 ml), followed by the extraction with a 4:1-mixture of dichloromethane and methanol. The combined organic layers were washed with brine (200 ml), dried and evaporated at reduced pressure. After lyophilization the 5-cyclopropylmethoxy-pyrazine-2-carboxylic acid (34% yield) was obtained as a white solid. MS (ISP): m/z=195.0 [M+H]+.

後処理

  1. customFor the workup, the reaction mixture was quenched with an aqueous solution of citric acid (10%)
  2. extractionextracted with ethyl acetate (5×30 ml)
  3. extractionfollowed by the extraction with a 4
  4. washThe combined organic layers were washed with brine (200 ml)
  5. customdried
  6. customevaporated at reduced pressure

出典と根拠

ORDレコード
ord-cfd16c2651b8458482fea57fe387ded6
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115098B2

反応ノート

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