2,6-Lutidine → (s)-2,6-Dimethyl-6-triethylsilanyloxy-heptanal

HRID 493066Notes

Reaction equation

[OH:1][C:2]([CH3:11])([CH3:10])[CH2:3][CH2:4][CH2:5][C@H:6]([CH3:9])[CH:7]=[O:8].N1C(C)=CC=CC=1C.[Si:20](OS(C(F)(F)F)(=O)=O)([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22]>C(Cl)Cl>[CH3:9][C@@H:6]([CH2:5][CH2:4][CH2:3][C:2]([CH3:10])([O:1][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:11])[CH:7]=[O:8]

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of aldehyde 9 (93.4 mg, 0.6 mmol) and 2,6-lutidine (170 μL, 1.5 mmol) in anhydrous CH2Cl2 (3.7 mL) was added dropwise Et3SiOTf (161 μL, 0.72 mmol) at 0° C. under argon. The solution was stirred at 10° C. for 3 hours and then at room temperature for 30 minutes. The mixture was quenched with cold water and extracted with CH2Cl2. The solvent was removed under reduced pressure, and the residue was chromatographed on silica Sep-Pak cartridge using hexane/EtOAc (99.7:0.3) as an eluent to give an oily aldehyde 10 (130 mg, 81%).

Workup

waitat room temperature for 30 minutes
customThe mixture was quenched with cold water
extractionextracted with CH2Cl2
customThe solvent was removed under reduced pressure
customthe residue was chromatographed on silica Sep-Pak cartridge

Sources & evidence

ORD record: ord-a95674b6a51844edbe46929167ead3b0
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534777B2

Reaction notes

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