Triethyl phosphonoacetate → ethyl (E)-4-(2,2,3,3-tetrafluoropropoxy)cinnamate

反応式

[F:1][C:2]([F:16])([CH:13]([F:15])[F:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#N)=[CH:7][CH:6]=1.[H-].C([Al+]CC(C)C)C(C)C.FC(F)(C(F)F)COC1C=CC(C=O)=CC=1.C(OP([CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])(OCC)=O)C>>[F:1][C:2]([F:16])([CH:13]([F:15])[F:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:51]/[C:52]([O:54][CH2:55][CH3:56])=[O:53])=[CH:7][CH:6]=1

参加物

反応物 4

HCID 13345Triethyl phosphonoacetate

HCID 117466214-(2,2,3,3-Tetrafluoropropoxy)benzaldehyde2 回

HCID 21225700Diisobutylaluminumhydride

HCID 290047704-(2,2,3,3-Tetrafluoropropoxy)benzonitrile

生成物 1

HCID 10686071ethyl (E)-4-(2,2,3,3-tetrafluoropropoxy)cinnamate

実験手順

In a first step, p-chlorobenzonitrile is reacted with 2,2,3,3-tetrafluoropropanol in the presence of bases, for example sodium hydride, with exchange of the p-chlorine atom to give 4-(2,2,3,3-tetrafluoropropoxy)benzonitrile. The second step is to reduce the 4-(2,2,3,3-tetrafluoropropoxy)benzonitrile by metal hydrides, for example diisobutylaluminum hydride, 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde being formed. The 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde is reacted stereoselectively with ethyl diethylphosphonoacetate in a third reaction step to give ethyl (E)-4-(2,2,3,3-tetrafluoropropoxy)cinnamate.