Nitrogen → [5-(tert-Butyl-dimethyl-silanyloxymethyl)-isoxazol-3-yl]-methanol
Reaction equation
N#N.C([O:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]([CH3:21])([CH3:20])[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[O:10][N:9]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[C:16]([SiH2:15][O:14][C:13]([CH3:21])([CH3:20])[C:11]1[O:10][N:9]=[C:8]([CH2:6][OH:5])[CH:12]=1)([CH3:19])([CH3:17])[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(tert-butyl-dimethyl-silanyloxymethyl)-isoxazole-3-carboxylic acid ethyl ester (5.77 g, 20.22 mmol) in THF (200 mL) was treated at −78° C. with DiBAL-H (40.00 mL of a 1M solution in THF, 40.43 mmol). The reaction mixture was stirred at this temperature for 1 h before to be allowed to warm to rt. The reaction mixture was poured onto Rochelle's salt (200 mL) and stirred at rt for 1 h. The aq. layer was extracted with EA (2×200 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (70:30 hept-EA) gave the title compound as a yellow oil: TLC:rf (70:30 hept-EA)=0.28. LC-MS-conditions 02: tR=0.99 min; [M+H]+=244.35.
Workup
- additionThe reaction mixture was poured onto Rochelle's salt (200 mL)
- stirringstirred at rt for 1 h
- extractionThe aq. layer was extracted with EA (2×200 mL)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the residue by FC (70:30 hept-EA)
Sources & evidence
- ORD record
- ord-4f2786b327cd44d2977e6c41819cef5a
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536209B2
Reaction notes
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