Hydrochloric Acid → 2,6-Dichloro-4-[(triisopropylsilyl)oxy]methylbenzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9].C([Li])CCC.CN(C)[CH:28]=[O:29].Cl.[Na+].[Cl-]>O1CCCC1>[Cl:20][C:18]1[CH:17]=[C:4]([CH2:5][O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:8]([CH3:9])[CH3:10])[CH:11]([CH3:12])[CH3:13])[CH:3]=[C:2]([Cl:1])[C:19]=1[CH:28]=[O:29]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
[(3,5-Dichlorobenzyl)oxy](triisopropyl)silane (14.8 g, 44.4 mmol) was stirred in tetrahydrofuran (30 mL) and cooled to −78° C. A solution of n-butyllithium (30.5 mL, 1.6 M in hexane, 48.8 mmol) was added dropwise and the mixture was stirred at −78° C. for 1 hour. N,N-dimethylformamide (4.47 mL, 57.7 mmol) was added and the mixture was allowed to warm to room temperature. A solution of 1 N HCl saturated with NaCl (15 mL) was added. The organic layer was separated and concentrated. The crude product was purified by chromatography on silica gel eluting with hexane to 10% ethyl acetate/hexane. Pure fractions were combined and concentrated to provide the desired product as a white solid (13.0 g, 81%). 1H NMR (CDCl3) δ 10.43 (s, 1H), 7.39 (s, 2H), 4.80 (s, 2H), 1.18 (m, 3H), 1.03 (s, 18H). LC/MS: 361 (M+H)+.
Workup
- temperatureto warm to room temperature
- customThe organic layer was separated
- concentrationconcentrated
- customThe crude product was purified by chromatography on silica gel eluting with hexane to 10% ethyl acetate/hexane
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1a4eda7521f04225abadc133dd6d7dd3
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563541B2
Reaction notes
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