Nitrogen → HCID 131730008, compound

HRID 42851Notes

Reaction equation

HRID 42851 reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:18])([CH3:17])[C:10]1[O:11][CH:12]=[C:13]([CH:15]=[O:16])[N:14]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:19][Al](C)C.[NH4+].[Cl-]>C(Cl)Cl.C1(C)C=CC=CC=1>[C:3]([SiH2:7][O:8][C:9]([CH3:18])([CH3:17])[C:10]1[O:11][CH:12]=[C:13]([CH:15]([OH:16])[CH3:19])[N:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 131730006HCID 131730006, compound

Product 1

HCID 131730008HCID 131730008, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

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 2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole-4-carbaldehyde (223 mg, 0.92 mmol) in CH2Cl2 (8.0 mL) was treated at 0° C. with trimethylaluminum (2.50 mL of a 2M solution in toluene, 5.00 mmol). The reaction mixture was then stirred at 0° C. for 45 min. Sat. aq. NH4Cl was then added and the aq. layer was extracted twice with CH2Cl2 and twice with EA. The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a colorless oil. TLC:rf (1:1 hept-EA)=0.32. LC-MS-conditions 02: tR=0.97 min, [M+H]+=258.30.

Workup

  1. extractionthe aq. layer was extracted twice with CH2Cl2 and twice with EA
  2. dry with materialextracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-ce1713bf663544b4aaab0514b2b152c9
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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