Dimethylformamide → 4-(Tert-butyl-dimethyl-silanyloxy)-2-isopropyl-benzaldehyde

HRID 395198Notes

Reaction equation

Br[C:2]1[CH:15]=[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[CH:16]([CH3:18])[CH3:17].C([Li])(C)(C)C.CN([CH:27]=[O:28])C>CCCCC.O>[C:10]([Si:7]([CH3:9])([CH3:8])[O:6][C:5]1[CH:14]=[CH:15][C:2]([CH:27]=[O:28])=[C:3]([CH:16]([CH3:18])[CH3:17])[CH:4]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of (4-bromo-3-isopropyl-phenoxy)-tert-butyl-dimethyl-silane (Intermediate 145, 1.03 g, 3.13 mmols) in 25 mL E20 was cooled to −78° C. and treated with tert-butyllithium (401.0 mg, 6.26 mmols; 3.7 mL of a 1.7M solution in pentane). After 30 minutes the reaction was quenched with DMF (913.0 mg, 12.5 mmols) and warmed to room temperature. The solution was diluted with H2O, extracted with Et2O and the combined organic layers washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. Column chromatography (2% EtOAc-hexanes) afforded 480.0 mg (55%) of the title compound as a colorless oil.

Workup

temperaturewarmed to room temperature
extractionextracted with Et2O
washthe combined organic layers washed with H2O and saturated aqueous NaCl
dry with materialbefore being dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-90d28ec1533f488ebd47120f5f7b9b42
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603019B2

Reaction notes

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