Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | HCID 131730007 | HCID 131730007 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 131730006 | HCID 131730006 | — |
Reaction Steps
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole-4-carboxylic acid ethyl ester (283 mg, 0.99 mmol) in CH2Cl2 (5.0 mL) was treated at −78° C. with DiBAL (1.85 mL of a 1M sol in toluene, 1.85 mmol) and the reaction mixture was stirred for 1 h at −78° C. MeOH (70 μL) and H2O (100 μL) were added and the reaction mixture was allowed to warm to rt. The reaction mixture was filtered, and the solvent removed under reduced pressure to give the title compound as a colorless oil. TLC:rf (1:1 hept-EA)=0.61. LC-MS-conditions 02: tR=1.03 min; [M+H2O+H]+=260.50.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08536209B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-f3280cacb6ff45c68cdc023e8a0a3857 |
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| Source note | uspto-grants-2013_09 |
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