Trifluoroacetic acid → Ethyl 5-oxooctahydropentalene-2-carboxylate

HRID 520391

反応式

HRID 520391 の反応式
[O:1]=[C:2]1[CH2:9][CH:8]2[CH:4]([CH2:5][C:6](C(OCC)=O)([C:10]([O:12][C:13](C)(C)[CH3:14])=[O:11])[CH2:7]2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][CH:4]2[CH:8]([CH2:7][CH:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:5]2)[CH2:9]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86690104HCID 86690104、化合物

生成物 1

HCID 73030532Ethyl 5-oxooctahydropentalene-2-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-tert-butyl 2-ethyl 5-oxohexahydropentalene-2,2(1H)-dicarboxylate (0.8 g, 2.70 mmol) in DCM (4 mL) was added TFA (2.080 mL) and the reaction mixture was stirred at rt for 4 h. The reaction mixture was evaporated to dryness and the residue was dissolved in pyridine (5 mL) and heated to reflux for 4 h until decarboxylation was complete. Pyridine was evaporated and the residue was purified by silica gel chromatography (10% EtOAC in DCM) to afford ethyl 5-oxooctahydropentalene-2-carboxylate (a mixture of endo/exo isomers) as a clear oil. 1H NMR (500 MHz, CDCl3) δ ppm 4.10-4.18 (2H, m), 2.85-3.02 (2H, m), 2.69-2.80 (1H, m), 2.44-2.56 (2H, m), 2.20-2.36 (2H, m), 2.10-2.20 (1H, m), 2.04 (1H, dd, J=19.45, 4.65 Hz), 1.66-1.80 (2H, m), 1.22-1.31 (3H, m).

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in pyridine (5 mL)
  3. temperatureheated
  4. temperatureto reflux for 4 h until decarboxylation
  5. customPyridine was evaporated
  6. customthe residue was purified by silica gel chromatography (10% EtOAC in DCM)

出典と根拠

ORDレコード
ord-2775b74e14354afda0777932d703f284
出典データセット
uspto-grants-2016_05
特許番号
US09326973B2

関連ノート

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