HCID 12647858, compound → HCID 13049518, compound

HRID 641378Notes

Reaction equation

HRID 641378 reaction equation
[C:1]([CH2:4][C:5]1([C:14]([OH:16])=[O:15])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([OH:3])=O>C(Cl)(=O)C>[CH2:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]21[CH2:4][C:1](=[O:3])[O:16][C:14]2=[O:15]

Participants

3

Reactant 1

HCID 12647858HCID 12647858, compound

Product 1

HCID 13049518HCID 13049518, compound

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

A solution of 2-(carboxymethyl)indane-2-carboxylic acid from Step C (1.10 g, 4.99 mmol) in acetyl chloride (18 mL) was heated at reflux for 18 h, then concentrated in vacuo. The residue was recrystallized from toluene to give 1′,3′-dihydrospiro[furan-3,2′-indene]-2,5(4H)-dione as an ivory solid. This solid was dissolved in CH2Cl2 (25 mL) and NH3 (g) was bubbled into the mixture for 20 min. After a further 30 min, the solvent was evaporated under reduced pressure. The resulting solid was dried under high vacuum for 1 h, then resuspended in acetyl chloride (20 mL) and heated to reflux for 18 h. The solvent was removed in vacuo and the crude solid was recrystallized from EtOH:Et2O to afford the title compound. MS: m/z=202 (M+1).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-148b89a7f07d4d3fa7a43d9e1548d729
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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