Water → HCID 18454512, compound

HRID 1271697Notes

Reaction equation

HRID 1271697 reaction equation
[CH:1](/[C:9]1[CH:10]=[CH:11][C:12]2[O:13][CH2:14][C:15](=O)[NH:16][C:17]=2[N:18]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.CCOCC>[CH:1](/[C:9]1[CH:10]=[CH:11][C:12]2[O:13][CH2:14][CH2:15][NH:16][C:17]=2[N:18]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21873663HCID 21873663, compound

Product 1

HCID 18454512HCID 18454512, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

6-((E)-Styryl)-4H-pyrido[3,2-b][1,4]oxazin-3-one (30d) (350 mg, 1.54 mmole), was dissolved in anhydrous THF (10 mL) and the solution was cooled to 0° C. A solution of LiAlH4 in THF (1.0 M, 1.54 mL, 1.54 mmole) was added dropwise at 0° C. The reaction was then warmed to room temperature and stirred for 2 hr. H2O (0.06 mL) was added dropwise and mixture was stirred for 5 min, then 15% sodium hydroxide (0.06 mL) was added followed by H2O (0.18 mL). The mixture was stirred overnight, then was diluted with Et2O and filtered through celite®. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (5% EtOAc/CHCl3) to afford the product (200 mg, 55%).

Workup

  1. temperatureThe reaction was then warmed to room temperature
  2. stirringmixture was stirred for 5 min
  3. stirringThe mixture was stirred overnight
  4. filtrationfiltered through celite®
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (5% EtOAc/CHCl3)

Sources & evidence

ORD record
ord-508029176c0c437b98bd887ccd019c36
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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