2-Nitrobenzaldehyde → HCID 53420451, compound
Reaction equation
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].[N+:7]([C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13])([O-:9])=[O:8]>CCCCCC.O1CCCC1>[N+:7]([C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]([OH:13])[C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])([O-:9])=[O:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -76 °C
Procedure
Into a round-bottomed flask was placed ethynyltrimethylsilane (4.90 mL), and tetrahydrofuran (THF) and was cooled to −76° C. A solution of 2.0 M n-butullithium in hexane (15.8 mL) was added dropwise. The reaction mixture was stirred at −76° C. for 30 minutes and a solution of o-nitrobenzaldehyde (3.0 g) in anhydrous THF was added. The reaction mixture was stirred at −76° C. for 60 minutes, and quenched with water. The reaction mixture was warmed up to room temperature and THF was removed under vacuum. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated to dryness. The crude material was purified by chromatography on silica gel giving a yield of 4.3 grams (87%).
Workup
- customInto a round-bottomed flask was placed
- stirringThe reaction mixture was stirred at −76° C. for 60 minutes
- customquenched with water
- temperatureThe reaction mixture was warmed up to room temperature
- customTHF was removed under vacuum
- extractionThe aqueous phase was extracted with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulfate
- customevaporated to dryness
- customThe crude material was purified by chromatography on silica gel giving a yield of 4.3 grams (87%)
Sources & evidence
- ORD record
- ord-2c03b93a50094880b4e300e9cbb0022d
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722886B1
Reaction notes
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