Hydrochloric Acid → 5-(3-((t-Butyldimethylsilyl)oxy)propyl)thiophene-2-carbaldehyde
Reaction equation
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CN(C)[CH:24]=[O:25].Cl>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[Si:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]1[S:11][C:12]([CH:24]=[O:25])=[CH:13][CH:14]=1)([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:15])[CH3:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of tert-butyldimethyl(3-(thiophen-2-yl)propoxy)silane (787 mg, 3.07 mmol) in 15 mL 9:1 tetrahydrofuran/hexamethylphosphoramide under argon at −78° C. was added n-butyllithium (1.35 mL, 2.5 M in hexanes) dropwise over 5 minutes. The resulting solution was stirred at −78° C. for 1 h. Dimethylformamide (1.18 mL, 15.35 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature before being poured into 100 mL of 1 N hydrochloric acid. Organics were extracted with ether (2×75 m), dried over magnesium sulfate, filtered and concentrated to give crude 5-(3-((t-butyldimethylsilyl)oxy)propyl)thiophene-2-carbaldehyde. Used without further purification.
Workup
- temperatureto warm to room temperature
- extractionOrganics were extracted with ether (2×75 m)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c83a20339b81439f920d6880374ac04d
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315495B2
Reaction notes
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