Ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate → 2-(2-oxocyclopentyl)acetic Acid

HRID 62799

反応式

HRID 62799 の反応式
C([O:3][C:4](=[O:17])[CH2:5][C:6]1(C(OCC)=O)[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])C>CC(O)=O.Cl>[O:11]=[C:7]1[CH2:8][CH2:9][CH2:10][CH:6]1[CH2:5][C:4]([OH:17])=[O:3]

参加物

4

反応物 1

HCID 4418640Ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate

生成物 1

HCID 35699832-(2-oxocyclopentyl)acetic Acid収率 75.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒

実験手順

A solution of ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate (50.0 g, 206 mmol) in HOAc (500 mL) and 6 M HCl (250 mL) was heated at 100° C. for 6 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (500 mL) and H2O (200 mL). Aqueous layer was separated and extracted with EtOAc (2×250 mL). The combined organic layers were washed with H2O (300 mL), brine (300 mL), dried over Na2SO4, decanted and concentrated to yield the title compound as a white solid (22 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.59-1.72 (m, 1H), 1.75-1.90 (m, 1H), 2.03-2.10 (m, 1H), 2.20 (dd, J=10.9, 8.9 Hz, 1H), 2.30-2.40 (m, 2H), 2.40-2.50 (m, 2H), 2.80 (dd, J=15.7, 7.2 Hz, 1H), 11.5 (s, 1H).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (500 mL) and H2O (200 mL)
  3. customAqueous layer was separated
  4. extractionextracted with EtOAc (2×250 mL)
  5. washThe combined organic layers were washed with H2O (300 mL), brine (300 mL)
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4505539facc24cffac6611ec5bf7f76f
出典データセット
uspto-grants-2016_09
特許番号
US09447041B2

関連ノート

読み込み中…