Trifluoroacetic acid → Ethyl (E)-4,4-difluoropent-2-enoate

HRID 631793ノート

反応式

HRID 631793 の反応式
[F:1][C:2]([F:12])([CH3:11])[CH:3](O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CN=2)C=CC=CC=1.FC(F)(F)C(O)=O>C1COCC1>[F:1][C:2]([F:12])([CH3:11])/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 6218932-PyridyldiphenylphosphineHCID 89825740Ethyl 4,4-difluoro-3-hydroxy-pentanoate

生成物 1

HCID 118534660Ethyl (E)-4,4-difluoropent-2-enoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl 4,4-difluoro-3-hydroxy-pentanoate (3.39 g, 0.0186 mol) was dissolved in THF (20 ml). Diphenyl-2-pyridylphosphin (7.37 g, 0.028 mol) was added followed after five minutes by di-tertbutylazodicarboxylate (2.83 g, 0.028 mol). The mixture was stirred for one hour at room temperature and left standing overnight. The mixture was acidified with trifluoroacetic acid (2 ml) and stirred for one hour at room temperature. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and 4N HCl. The phases were separated, the organic phase was washed with 1M HCl (4×), dried over magnesium sulfate and evaporated to dryness. After distillation at 2 mbar 5.99 g were obtained which still contained some solvent but were used directly in the next step.

後処理

  1. waitleft
  2. waitstanding overnight
  3. stirringstirred for one hour at room temperature
  4. customThe solvent was removed under reduced pressure
  5. customthe residue partitioned between ethyl acetate and 4N HCl
  6. customThe phases were separated
  7. washthe organic phase was washed with 1M HCl (4×)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. distillationAfter distillation at 2 mbar 5.99 g
  11. customwere obtained which

出典と根拠

ORDレコード
ord-d618082ccc9f4e30af60d03b752022ae
出典データセット
uspto-grants-2016_04
特許番号
US09321724B2

反応ノート

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