2-Methyl-2-butene → 1-(2-Bromopyridin-4-yl)cyclopropane-1-carboxylic acid

HRID 1423069ノート

反応式

HRID 1423069 の反応式
Cl([O-])=O.[Na+].[OH2:5].P([O-])(O)(O)=O.[Na+].[Br:12][C:13]1[CH:18]=[C:17]([C:19]2([CH:22]=[O:23])[CH2:21][CH2:20]2)[CH:16]=[CH:15][N:14]=1.CC(=CC)C>O.C(O)(C)(C)C>[Br:12][C:13]1[CH:18]=[C:17]([C:19]2([C:22]([OH:5])=[O:23])[CH2:20][CH2:21]2)[CH:16]=[CH:15][N:14]=1

参加物

7

反応物 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 866727561-(2-Bromo-4-pyridinyl)cyclopropanecarboxaldehyde

生成物 1

HCID 717432461-(2-Bromopyridin-4-yl)cyclopropane-1-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

A solution of sodium chlorite (368 mg, 3.26 mmol) and sodium dihydrogen phosphate monohydrate (449 mg, 3.26 mmol) in 5 mL of water is added dropwise to a solution of crude 1-(2-bromopyridin-4-yl)-cyclopropanecarboxaldehyde (566 mg, 2.50 mmol) and 2-methyl-2-butene (1.73 mL, 16.3 mmol) in t-butanol (12 mL), and the resulting reaction mixture is stirred at room temperature. After 18 hours, the mixture is concentrated in vacuo, acidified to pH 2 with 1 M aqueous HCl, diluted with brine (25 mL) and extracted with EtOAc (3×50 mL). The combined organic layers are dried over Na2SO4, filtered and concentrated to afford crude 1-(2-bromopyridin-4-yl)-cyclopropanecarboxylic acid which is used without purification.

後処理

  1. customthe resulting reaction mixture
  2. concentrationthe mixture is concentrated in vacuo
  3. additiondiluted with brine (25 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2f52ecc95e7145a5b7755525fa9d037f
出典データセット
uspto-grants-2015_01
特許番号
US08927550B2

反応ノート

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