Water → HCID 69134252, compound

HRID 969491Notes

Reaction equation

HRID 969491 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH2:8][CH2:9][CH:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:11][C:12]=2[C:13]2[N:17]=[C:16]([CH3:18])[N:15]([CH3:19])[C:14]=2[CH:20]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:18][C:16]1[N:15]([CH3:19])[C:14]2[CH:20]=[C:6]([CH2:4][OH:3])[C:7]3[CH2:8][CH2:9][CH:10]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:11][C:12]=3[C:13]=2[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69135072HCID 69135072, compound

Product 1

HCID 69134252HCID 69134252, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 mg (0.7 mmol) 2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid ethyl ester in 10 ml tetrahydrofuran was cooled to 0° C. and 927 μl (0.93 mmol) lithium aluminium hydride solution (1 M in THF) were added dropwise. The temperature was raised to room temperature and the reaction stirred for 1 h. To the reaction were cautiously added 1.5 ml water and 1.5 ml 6 M sodium hydroxide solution and the mixture was extracted with dichloromethane. The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=1:1) and crystallized with diisopropyl ether to afford 101 mg (45%) of the title compound as a beige solid. m.p. 279°-281° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic layers were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (toluene/dioxane=1:1)
  5. customcrystallized with diisopropyl ether

Sources & evidence

ORD record
ord-6ff93c8463a94e9cac9c36a517e2edb4
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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