Tetrahydrofuran → HCID 86591629、化合物

HRID 495460ノート

反応式

HRID 495460 の反応式
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[N+:19]([C:22]1[C:29](OC)=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][C:23]=1[CH:24]=O)([O-:21])=[O:20].[NH4+].[Cl-].C1C[O:39][CH2:38]C1>O>[CH2:4]([O:5][C:6](=[O:7])[CH:8]=[CH:9][CH:10]=[CH:24][C:23]1[CH:26]=[C:27]([O:39][CH3:38])[C:28]([O:32][CH3:33])=[CH:29][C:22]=1[N+:19]([O-:21])=[O:20])[CH3:3]

参加物

7

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1524373,4-Dimethoxy-2-nitrobenzaldehydeHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

生成物 1

HCID 86591629HCID 86591629、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a suspension of NaH (0.24 g, 6.0 mmol) in THF (30 mL) at 0° C. was added a solution of triethyl 4-phosphonocrotonate (1.0 g, 4.0 mmol) in THF (5 mL) dropwise. The solution was warmed to RT and stirred for 1 h. Nitroveratraldehyde (0.844 g, 4.0 mmol) was added to the mixture in one portion and the reaction was stirred for an additional 30 min at RT. NH4Cl (aq., sat., 3 mL) was added slowly to quench the reaction, followed by H2O (30 mL). The THF solvent was removed under reduced pressure and the resulting mixture was extracted with EtOAc (3×10 mL). The organic extracts were combined, washed with brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the mixture was purified by chromatography on silica gel to afford the title compound.

後処理

  1. stirringthe reaction was stirred for an additional 30 min at RT
  2. customto quench
  3. customthe reaction
  4. customThe THF solvent was removed under reduced pressure
  5. extractionthe resulting mixture was extracted with EtOAc (3×10 mL)
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe mixture was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-e4c766c5234f499c9a39221c5686675d
出典データセット
uspto-grants-2005_09
特許番号
US06939874B2

反応ノート

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