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Water → HCID 18689383, compound

HRID 1871839
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Reaction equation

HRID 1871839 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=O)[N:20]=2)=[CH:11][CH:10]=1.[CH:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[C:27]1=O)[CH2:33]2.O>C1COCC1.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-].C(OCC)(=O)C>[CH:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[C:27]1=[C:19]1[C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[O:16][C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=3)=[N:20]1)[CH2:33]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 64151AdamantanoneHCID 776579HCID 776579, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18689383HCID 18689383, compound

Reagents, catalysts & solvents 3

HCID 160960Diamminetetrachlorotitanate(IV)
Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

21 mmol lithium aluminium hydride is carefully added to a suspension of 40 mmol titanium chloride in 100 ml absolute THF while stirring vigorously. After stirring for 1 hour at room temperature, a mixture of 15 mmol 2-(4'-methoxyphenyl)-4H-1,3-benzoxazine-4-one and 11 mmol adamantanone is added while cooling on ice. It is heated to boiling for 60 min under reflux. After cooling to room temperature it is poured onto 200 ml water. The mixture is shaken out twice with 200 ml ethyl acetate each time. The combined organic phases are washed once with water and separated. After drying over sodium sulfate it is filtered and the solvent is removed by distillation. The oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:9).

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. additionis added
  3. temperaturewhile cooling on ice
  4. temperatureIt is heated
  5. temperatureunder reflux
  6. washThe combined organic phases are washed once with water
  7. customseparated
  8. dry with materialAfter drying over sodium sulfate it
  9. filtrationis filtered
  10. customthe solvent is removed by distillation
  11. customThe oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:9)

Sources & evidence

ORD record
ord-ff6363ccc5b945cfac88be3fee219ef2
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06107036

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes