Methanol → 2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde
Reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)[CH:27]=[O:28].O.CO>C(OCC)C>[CH2:18]([O:17][CH2:16][C:3]1[CH:4]=[C:5]([O:12][CH2:13][O:14][CH3:15])[CH:6]=[C:7]([O:8][CH2:9][O:10][CH3:11])[C:2]=1[CH:27]=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
The above-obtained 2-bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene (1.6 g, 4.3 mmol) was dissolved in diethylether (25 mL) and cooled to −78° C. The obtained solution was added with 1.52 mol/L n-butyllithium-hexane solution (4.0 mL, 6.1 mmol) and stirred at −78° C. for 1 hour. Then, N,N-dimethylformamide (1.0 mL, 13 mmol) was added thereto and stirred at a room temperature for 3 hours. The reaction mixture was added with water and methanol, and then extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, and then dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 to 5/1 to 3/1) to obtain 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde (0.99 g, 72%).
Workup
- additionThe obtained solution was added with 1.52 mol/L n-butyllithium-hexane solution (4.0 mL, 6.1 mmol)
- stirringstirred at a room temperature for 3 hours
- extractionextracted with chloroform 3 times
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThen the solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 to 5/1 to 3/1)
Sources & evidence
- ORD record
- ord-4f6fedc485ba409ca1005d609e123232
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781485B2
Reaction notes
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