Nitrogen → 1-(4-(((tert-Butyldimethylsilyl)oxy)methyl)oxazol-2-yl)ethanol

HRID 82818Notes

Reaction equation

N#N.[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([CH:17]=[O:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:19][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]([CH:17]([OH:18])[CH3:19])[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 4-(((tert-butyldimethylsilyl)oxy)methyl)oxazole-2-carbaldehyde (268 mg, 1.11 mmol) in CH2Cl2 (9.2 mL) was treated dropwise at 0° C. with trimethylaluminium (1.11 mL of a 2.0 M solution in toluene, 2.22 mmol) and the resulting yellow solution was stirred for 45 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. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:1 hept-EA)=0.40. LC-MS-conditions 07: tR=0.85 min, [M]+=257.81.

Workup

extractionwas extracted with CH2Cl2 (3×25 mL)
dry with materiallayers were dried over Na2SO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record: ord-5fe46aa6a2c74727a6ceb85673259450
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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