Water → 2-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde
Reaction equation
C1(S[C:8]2([O:11][C:12]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][C:13]=3[CH:14]=[O:15])[CH2:10][CH2:9]2)C=CC=CC=1.[C-]1C2C(=CC=CC=2)C=CC=1.[Li+].O>C1COCC1>[CH:8]1([O:11][C:12]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:16][C:13]=2[CH:14]=[O:15])[CH2:10][CH2:9]1Participants
Procedure
Freshly cut lithium metal (97 mg, 13.9 mmol) was added to a solution of naphthalene (1.77 g, 13.9 mmol) in THF (20 mL) and the mixture was sonicated at room temperature for 30 min. to produce a dark green solution of lithium naphthalenide. A solution of 2-(1-phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehyde (Description 1, 96 mg, 0.27 mmol) in THF (2 mL) was cooled to -78° C. and the solution of lithium naphthalenide in THF (2 mL) was added dropwise until the intense green colour persisted. The reaction was then stirred for 5 min., water (6 mL) was added and the mixture was warmed to room temperature. The mixture was extracted with ethyl acetate, the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (80:20), to give to give the title compound as a colourless oil (4 mg, 6%). 1H NMR (360 MHz, CDCl3) δ0.86 (4H, m), 3.82-3.9 (1H, m), 7.42 (2H, m), 7.62 (1H, d, J 2.5 ) Hz), and 10.36 (1H, s).
Workup
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe combined organic fractions were dried (MgSO4)
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
- washeluting with hexane/Et2O (80:20)
- customto give
Sources & evidence
- ORD record
- ord-1cf4ea80aef649c4a5bc14fc86942bfa
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06156749
Reaction notes
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