Dimethylformamide → 4-[(Tert-butyldimethylsilyl)oxy]-2,6-dimethylbenzaldehyde

HRID 1514999Notes

Reaction equation

Br[C:2]1[C:15]([CH3:16])=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][C:3]=1[CH3:17].C[Li].[Li+].[Br-].[Li]C(CC)C.CN([CH:30]=[O:31])C>C1COCC1.CCOCC.C1CCCCC1>[C:10]([Si:7]([CH3:9])([CH3:8])[O:6][C:5]1[CH:14]=[C:15]([CH3:16])[C:2]([CH:30]=[O:31])=[C:3]([CH3:17])[CH:4]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (4-bromo-3,5-dimethylphenoxy)-tert-butyl-dimethylsilane (3.1 g, 9.8 mmol) in THF (30 mL) at −78° C. under N2 protection was added dropwise methyllithium/LiBr (9.3 ml of a 1.5 M solution in Et2O, 14 mmol). After 5 min of stirring, sec-BuLi (10 mL of a 1.4 M solution in cyclohexane, 14 mmol) was added slowly to the reaction solution at −78° C. After 5 min, anhydrous DMF (1.5 mL, 20 mmol) was added slowly then the solution was warmed to 25° C. After 30 min, the reaction mixture was quenched with water. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (6:1) to give 4-(tert-butyldimethyl-silanyloxy)-2,6-dimethylbenzaldehyde as a yellow oil.

Workup

waitAfter 5 min
waitAfter 30 min
customthe reaction mixture was quenched with water
extractionThe aqueous layer was extracted with CH2Cl2
washthe combined organic layers were washed with water, brine
dry with materialdried with MgSO4
filtrationfiltered
customThe solvent was removed under reduced pressure
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-aaf1d1901f9146929e9a35c4b2658087
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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