Nitrogen → 2-(4-(((tert-Butyldimethylsilyl)oxy)methyl)oxazol-2-yl)propan-2-ol

HRID 82820Notes

Reaction equation

N#N.[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17](=[O:19])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:20][Al](C)C.[NH4+].[Cl-]>C(Cl)Cl.C1(C)C=CC=CC=1>[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17]([OH:19])([CH3:20])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(4-(((tert-butyldimethylsilyl)oxy)methyl)oxazol-2-yl)ethanone (171 mg, 0.67 mmol) in CH2Cl2 (5.6 mL) was treated dropwise at 0° C. with trimethylaluminium (0.56 mL of a 2.0 M solution in toluene, 1.12 mmol) and the resulting yellow solution was stirred for 90 min at 0° C. Sat. aq. NH4Cl was added to the reaction mixture which was extracted with CH2Cl2 (3×25 mL) and the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.88 min, [M+H]+=272.20.

Workup

extractionwas extracted with CH2Cl2 (3×25 mL)
dry with materiallayers were dried over Na2SO4
filtrationfiltered
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a5a75dfe6036436da913e555a7f495b6
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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