Acetic Acid → 1-(5-Iodopyridin-2-YL)cyclobutanecarboxylic acid

HRID 2038756ノート

反応式

HRID 2038756 の反応式
[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH2:14].CC(O)=[O:17].S(=O)(=O)(O)O>CCOCC>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]([OH:17])=[O:14])[CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962Water2 回HCID 1118Sulfuric AcidHCID 708006921-(5-Iodopyridin-2-YL)cyclobutanecarbonitrile

生成物 1

HCID 675084441-(5-Iodopyridin-2-YL)cyclobutanecarboxylic acid

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
115 °C

実験手順

1-(5-Iodo-pyridin-2-yl)-cyclobutane carbonitrile (4.0 g, 14 mmol) was combined with water (5.0 mL), glacial AcOH (5.0 mL) and concentrated sulfuric acid (5.0 mL). The homogeneous solution was heated to reflux (external bath: 115° C.). After 5 h, the solution was cooled to room temperature and poured into water (10 mL) and Et2O (15 mL). The layers were separated and the Et2O layer was discarded. The aqueous layer was adjusted to pH 4.5-5 by the addition of 2M aq. NaOH and then extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 layers were washed with brine, dried over MgSO4, filtered and concentrated to yield 3.92 g of 1-(5-iodo-pyridin-2-yl)-cyclobutane carboxylic acid, m/z 304.4 [M+H]+.

後処理

  1. temperatureThe homogeneous solution was heated
  2. temperaturethe solution was cooled to room temperature
  3. customThe layers were separated
  4. additionThe aqueous layer was adjusted to pH 4.5-5 by the addition of 2M aq. NaOH
  5. extractionextracted with CH2Cl2 (3×50 mL)
  6. washThe combined CH2Cl2 layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-6887ef12d60e4083bf32d557f34e150d
出典データセット
uspto-grants-2013_11
特許番号
US08575360B2

反応ノート

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