Water → 1-Methyl-3-methylidenecyclobutane-1-carboxylic acid
反応式
[OH-:1].[K+].[CH3:3][C:4]1([C:9]#N)[CH2:7][C:6](=[CH2:8])[CH2:5]1.[OH2:11]>CCO>[CH3:3][C:4]1([C:9]([OH:11])=[O:1])[CH2:7][C:6](=[CH2:8])[CH2:5]1参加物
5
実験手順
To a solution of KOH (12.0 g, 213 mmol) in water (10 mL) and EtOH (10 mL) was added 1-methyl-3-methylidenecyclobutanecarbonitrile (53.3 mmol, crude) and the resulting solution was heated to reflux for 2.5 hrs. The mixture was cooled to rt and the solvent was removed under vacuum. The residue was diluted with water (30 mL) and washed with EtOAc (30 mL). The aqueous layer was acidified with concentrated HCl to pH˜1 in ice bath, and then extracted with EtOAc (two×30 mL). The combined organics were dried over MgSO4 and concentrated to give the title compound acid as pale brown liquid. 1H NMR (400 MHz, chloroform-d) δ ppm 4.90 (quin, J=2.41 Hz, 2H), 3.16-3.34 (m, 2H), 2.54 (qd, J=2.10, 16.57 Hz, 2H), 1.49 (s, 3H).
後処理
- temperaturethe resulting solution was heated
- temperatureto reflux for 2.5 hrs
- customthe solvent was removed under vacuum
- additionThe residue was diluted with water (30 mL)
- washwashed with EtOAc (30 mL)
- extractionextracted with EtOAc (two×30 mL)
- dry with materialThe combined organics were dried over MgSO4
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-2b96e0dc5cbf47b5a4b727079d5b47fa
- 出典データセット
- uspto-grants-2015_05
- 特許番号
- US09040547B2
反応ノート
読み込み中…