Cyclopropanecarboxaldehyde → HCID 22993501, compound
Reaction equation
[CH:1](C1C2C(=CC=CC=2)C=C1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:27][NH2:28].C([Li])(C)(C)C.[CH:38]1([CH:41]=[O:42])[CH2:40][CH2:39]1>C1COCC1.CCOCC>[C:1](=[N:28][CH:27]([C:26]1[CH:29]=[CH:30][C:31]([F:32])=[C:24]([F:23])[CH:25]=1)[CH:41]([CH:38]1[CH2:40][CH2:39]1)[OH:42])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a solution of benzhydrylindene-(3,4-difluoro-benzyl)-amine (2.5 g, 8.1 mmol) in 50 mL of dry THF was added tert-butyllithium (1.7M, 6.2 mL) dropwise and the resulting solution was stirred at -78° C. for 0.5 h. To the solution was added cyclopropanecarboxaldehyde (0.90 ml, 12.0 mmol) in 10 ml of THF and the solution was stirred at -78° C. for 2 h and 25° C. for 1 h. The reaction was quenched by adding 1.0 mL of dilute acetic acid. Reaction mixture was diluted with 100 ml of Et2O and washed with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo, yielding 2-(benzhydryliden-amino)-1-cyclopropyl-2-(3,4-difluoro-phenyl)-ethanol as a yellow oil, which was subjected to the following reaction without purification.
Workup
- stirringthe solution was stirred at -78° C. for 2 h and 25° C. for 1 h
- customThe reaction was quenched
- additionby adding 1.0 mL of dilute acetic acid
- customReaction mixture
- washwashed with brine
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d37170c69e7a4dce8b91bb6bb00b3430
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06159990
Reaction notes
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