Methanol → HCID 131730006, compound

HRID 2040036Notes

Reaction equation

HRID 2040036 reaction equation
N#N.C([O:5][C:6]([C:8]1[N:9]=[C:10]([C:13]([CH3:21])([CH3:20])[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[O:11][CH:12]=1)=O)C.CC(C[AlH]CC(C)C)C.CO>C(Cl)Cl.C1(C)C=CC=CC=1.O>[C:16]([SiH2:15][O:14][C:13]([CH3:21])([CH3:20])[C:10]1[O:11][CH:12]=[C:8]([CH:6]=[O:5])[N:9]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 887MethanolHCID 947NitrogenHCID 14487Diisobutylaluminum hydrideHCID 131730007HCID 131730007, compound

Product 1

HCID 131730006HCID 131730006, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °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-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.

Workup

  1. temperatureto warm to rt
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-25608acc5df14069aa41aa5c6356c946
Source dataset
uspto-grants-2013_11
Patent number
US08580831B2

Reaction notes

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