HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethyl orthoformate → 6H-Indeno[5,4-d]oxazol-8(7H)-one

HRID 1039262
Notes
Print preview

Reaction equation

HRID 1039262 reaction equation
Br.[NH2:2][C:3]1[C:11]([OH:12])=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:13])=[CH:5][CH:4]=1.[CH:14](OCC)(OCC)OCC>O1CCCC1.C(OCC)(=O)C>[O:12]1[C:11]2[C:10]3[C:9](=[O:13])[CH2:8][CH2:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:2]=[CH:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 673534616-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromide

Product 1

HCID 577812656H-Indeno[5,4-d]oxazol-8(7H)-oneYield 362%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Amino-7-hydroxyindan-1-one hydrobromide (50 mg, 0.205 mmol) and triethyl orthoformate (128 μL, 0.769 mmol) were heated under reflux in tetrahydrofuran (2.5 mL) for 0.5 hr. The mixture was diluted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (21.9 mg, yield from Reference Example 362%).

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20)

Sources & evidence

ORD record
ord-69c721992215426d8f732c899ff32d4d
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552037B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes