2-(Triisopropylsilyl)oxazole-5-carboxaldehyde → HCID 57771144, compound

HRID 1773584Notes

Reaction equation

HRID 1773584 reaction equation
B.[Na].[CH:3]([Si:6]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[C:7]1[O:8][C:9]([CH:12]=[O:13])=[CH:10][N:11]=1)([CH3:5])[CH3:4]>CO.N1C=CC=CC=1.O.C(OCC)(=O)C>[CH:17]([Si:6]([CH:3]([CH3:5])[CH3:4])([CH:14]([CH3:16])[CH3:15])[C:7]1[O:8][C:9]([CH2:12][OH:13])=[CH:10][N:11]=1)([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 117158052-(Triisopropylsilyl)oxazole-5-carboxaldehydeHCID 178418435HCID 178418435, compound

Product 1

HCID 57771144HCID 57771144, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 66926435Pyridine waterSolvent

Procedure

Sodiumboron hydride (200 mg, 5.5 mmol) was added to a solution of 2-triisopropylsilyl-oxazole-5-carboxaldehyde (0.7 g, 2.7 mmol) in a mixture of methanol and tetrahydrofuran (1/1, 20 mL) and the resulting mixture was stirred at room temperature for 20 minutes. The reaction mixture was then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give (2-triisopropylsilanyl-oxazol-5-yl)-methanol without further purifications. This material was treated with 4-chloro-2-nitro-phenol as described in Preparation 20, Step A, to give 0.7 g of 5-(4-chloro-2-nitro-phenoxymethyl)-2-triisopropylsilanyl-oxazole.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dfb04480f8614d3da80e4d356a7c3cf0
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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