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

HRID 1597026Notes

Reaction equation

HRID 1597026 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

6

Reactant 3

HCID 6228DimethylformamideHCID 22568908(4-Bromo-3-isopropyl-phenoxy)-tert-butyl-dimethyl-silane2×HCID 178418306HCID 178418306, compound

Product 1

HCID 225689004-(Tert-butyl-dimethyl-silanyloxy)-2-isopropyl-benzaldehydeYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8003PentaneSolvent

Procedure

A solution of (4-bromo-3-isopropyl-phenoxy)-tert-butyl-dimethyl-silane (Intermediate 145, 1.03 g, 3.13 mmols) in 25 mL E2O 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

  1. extractionextracted with Et2O
  2. washthe combined organic layers washed with H2O and saturated aqueous NaCl
  3. dry with materialbefore being dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b637091eb12143398ec94f2e3cf5b497
Source dataset
uspto-grants-2001_09
Patent number
US06291677B1

Reaction notes

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