Chloroform → {[tert-Butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetaldehyde
Reaction equation
[Si:1]([O:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10](OC)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Si:1]([O:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Participants
5
Conditions
- Temperature
- -78 °C
Procedure
Methyl {[tert-butyl(dimethyl)silyl]oxy}(4-methoxyphenyl)acetate (0.5 g, 1.61 mmol) was dissolved in toluene (10 mL) and cooled to −78° C. under a nitrogen atmosphere. DIBAL (1.0M in toluene, 1.9 mL, 1.93 mmol) was added slowly and the mixture was stirred at −78° C. for 1 h. The reaction mixture was poured onto a mixture of ice (20 g) and CHCl3 (20 mL). The mixture was stirred at r.t. for 30 minutes. The layers were separated and the water phase extracted with CHCl3. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated, obtaining 99% (0.45 g) of the title compound. The product was used directly in the next step without further purification.
Workup
- stirringThe mixture was stirred at r.t. for 30 minutes
- customThe layers were separated
- extractionthe water phase extracted with CHCl3
- washThe organic phase was washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8e50959f9d4047c59a60dde50e94b9d0
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829707B2
Reaction notes
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