Potassium Phosphate, Tribasic → 2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-cyclopropyl-benzaldehyde
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:21]1(B(O)O)[CH2:23][CH2:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O>[C:17]([Si:14]([CH3:16])([CH3:15])[O:13][CH2:12][CH2:11][O:10][C:5]1[CH:4]=[CH:3][C:2]([CH:21]2[CH2:23][CH2:22]2)=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:20])([CH3:19])[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 5-bromo-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-benzaldehyde (5 g, 13.9 mmol) prepared in example 130a in toluene (75 mL) and water (7.5 mL) was added cyclopropylboronic acid (1.7 g, 19.8 mmol) (Aldrich) and potassium phosphate (14.6 g, 68.9 mmol). After the reaction mixture was degassed for 5 min, dichloro-bis-(tricyclohexyl-phosphine) (1.03 g, 1.39 mmol) (Strem) was added and the reaction mixture was heated at 100° C. under nitrogen for 4 h. The reaction mixture was cooled to room temperature and diluted with water, extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified with chromatography to give 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-cyclopropyl-benzaldehyde as yellow oil (Yield: 3.2 g, 76.2%).
Workup
- customAfter the reaction mixture was degassed for 5 min
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate
- washwashed with water, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified with chromatography
Sources & evidence
- ORD record
- ord-d8ead33461d44ec98c0de7fc3ce69345
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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