Sulfuric Acid → HCID 59265941、化合物

HRID 909369ノート

反応式

HRID 909369 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2(O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][CH:9]=2)=[CH:6][N:7]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 592659571-(6-Chloro-pyridin-3-yl)cyclopentanol

生成物 1

HCID 59265941HCID 59265941、化合物収率 88%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

1-(6-Chloro-pyridin-3-yl)cyclopentanol (2.1 g, 10.5 mmol) was treated with acetic acid (12 mL) and sulfuric acid (4 mL) and the mixture heated to reflux for 30 min. After cooling to RT, ice and 2 N NaOH (180 mL) was add and the resulting tan precipitate collected by filtration, washed with H2O and dried giving 2-chloro-5-(cyclopent-1-enyl)pyridine (1.66 g, 88%) as a tan solid: mp 59-60° C., LC/MS (ESI) m/z 179, 1H NMR (300 MHz, CDCl3) δ 8.41 (d, 1H, J=2.4 Hz), 7.66 (dd, 1H, J=8.4, 2.4 Hz), 7.25 (d, 1H, J=8.4 Hz), 6.27 (t, 1H, J=2.1 Hz), 2.69 (bm, 2H), 2.55 (bm, 2H), 2.05 (m, 2H).

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux for 30 min
  3. filtrationthe resulting tan precipitate collected by filtration
  4. washwashed with H2O
  5. customdried

出典と根拠

ORDレコード
ord-ed5c98a6fb52410e9ec6c3f8e7022271
出典データセット
uspto-grants-2011_09
特許番号
US08017788B2

反応ノート

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