HCID 12194348、化合物 → HCID 70269233、化合物

HRID 1504393ノート

反応式

HRID 1504393 の反応式
[C@@H:1]12[O:7][C@@H:4]([CH:5]=[CH:6]1)[CH2:3][C@H:2]2[C:8]([O:10][CH2:11][CH3:12])=[O:9]>[Pd].C(O)C>[C@@H:1]12[O:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

4

反応物 1

HCID 12194348HCID 12194348、化合物

生成物 1

HCID 70269233HCID 70269233、化合物収率 92%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A flask was charged with (1R,2R,4R)-ethyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate (3.91 g, 23.25 mmol) and ethanol (35 mL). The solution was degassed with nitrogen for 5 minutes, then palladium on carbon (5 wt. % wet) (1.0 g, 0.470 mmol) was added portionwise. The flask was evacuated and backfilled three times with nitrogen, then evacuated and backfilled with hydrogen (balloon). The reaction was stirred overnight at room temperature. The reaction was filtered through a plug of Celite and washed several times with ethanol, making sure to keep the catalyst wet with solvent (a layer of sand was added after the first wash). The filtrate was concentrated to afford (1R,2R,4S)-ethyl 7-oxabicyclo[2.2.1]heptane-2-carboxylate (3.63 g, 21.33 mmol, 92% yield). 1H NMR (400 MHz, CHLOROFORM-d) S=4.82 (d, J=5.0 Hz, 1H), 4.72 (t, J=5.0 Hz, 1H), 4.66 (t, J=5.0 Hz, 1H), 4.63-4.59 (m, 1H), 4.22-4.10 (m, 3H), 3.08-2.97 (m, 1H), 2.59 (dd, J=4.9, 9.1 Hz, 1H), 2.14 (dtd, J=2.6, 5.0, 12.3 Hz, 1H), 1.95-1.87 (m, 1H), 1.83-1.63 (m, 4H), 1.62-1.41 (m, 3H), 1.34-1.21 (m, 4H)

後処理

  1. customThe solution was degassed with nitrogen for 5 minutes
  2. customThe flask was evacuated
  3. customevacuated
  4. filtrationThe reaction was filtered through a plug of Celite
  5. washwashed several times with ethanol
  6. additionwas added after the
  7. washfirst wash)
  8. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-f871a53b3d654a0e8ab1e68741f700bd
出典データセット
uspto-grants-2015_12
特許番号
US09212182B2

反応ノート

読み込み中…