E-methyl 6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hex-2-enoate → Methyl 6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hexanoate

HRID 1644148ノート

反応式

HRID 1644148 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]([OH:15])([C:11]([F:14])([F:13])[F:12])[CH2:4]/[CH:5]=[CH:6]/[C:7]([O:9][CH3:10])=[O:8]>[Pd].C(OCC)(=O)C>[F:1][C:2]([F:16])([F:17])[C:3]([OH:15])([C:11]([F:13])([F:14])[F:12])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

参加物

4

反応物 1

HCID 59429090E-methyl 6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hex-2-enoate

生成物 1

HCID 59429087Methyl 6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hexanoate収率 91%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a 330 mL thick-walled glass hydrogenation vessel was added 37.7 g E-methyl 6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hex-2-enoate (I) (141 mmol), 0.5 g palladium-on-carbon (5 wt % Pd), and 150 mL ethyl acetate. The reaction vessel was attached to a Parr hydrogenation apparatus and the reaction solution degassed via three successive pump-backfill cycles with nitrogen. The reaction vessel was pressurized to 40 psi with hydrogen and shaken at room temperature for 20 hours, after which the pressure had fallen to 34 psi. The excess hydrogen was removed via three successive pump-backfill cycles with nitrogen and the palladium catalyst removed via filtration through 1.0 micron glass fiber and 0.2 micron PTFE filters. The solvent was removed in vacuo and the crude reaction mixture distilled under vacuum (6 Torr, 64-74° C.) to afford 34.4 g (91%) of methyl 6,6,6-trifluoro-5-hydroxy-5-(trifluoromethyl)hexanoate (II) as a colorless liquid.

後処理

  1. customthe reaction solution degassed via three successive pump-backfill cycles with nitrogen
  2. customThe excess hydrogen was removed via three successive pump-backfill cycles with nitrogen
  3. customthe palladium catalyst removed via filtration through 1.0 micron glass fiber and 0.2 micron PTFE
  4. customThe solvent was removed in vacuo
  5. customthe crude reaction mixture
  6. distillationdistilled under vacuum (6 Torr, 64-74° C.)

出典と根拠

ORDレコード
ord-deb0bac976cb4c1f814c2538e8b60faf
出典データセット
uspto-grants-2012_02
特許番号
US08124327B2

反応ノート

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