Methyl formate → 3,5-Dichloro-4-pyridinecarboxaldehyde
Reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([Cl:20])[CH:19]=1.[CH:21](OC)=[O:22]>C1COCC1.Cl>[Cl:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([Cl:20])[C:19]=1[CH:21]=[O:22]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
n-Butyllithium (1.6M in hexanes, 9.3 ml, 14.9 mmol) was added dropwise at 0° C. to a solution of diisopropylamine (1.95 ml, 14.9 mmol) in THF (30 ml). After 15 min. at 0° C., the solution was cooled to −78° C. and 3,5-dichloropyridine (2.0 g, 13.5 mmol) was added. After 1 h, methyl formate (0.92 ml) was added and the mixture warmed to room temperature over 2 h, diluted with 1N hydrochloric acid and extracted twice with ethyl acetate. The extracts were washed with brine, dried over sodium sulphate and evaporated to give a yellow oil which solidified, m.p. 110-111° C.
Workup
- waitAfter 1 h
- temperaturethe mixture warmed to room temperature over 2 h
- extractionextracted twice with ethyl acetate
- washThe extracts were washed with brine
- dry with materialdried over sodium sulphate
- customevaporated
- customto give a yellow oil which
Sources & evidence
- ORD record
- ord-cbbe76755b7e405c9b756fe8f7b71fd6
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06303613B1
Reaction notes
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