Maleic Anhydride → HCID 58807382, compound

HRID 968983Notes

Reaction equation

HRID 968983 reaction equation
[CH3:1][CH:2]1[CH:10]2[CH:5](C3CC2C=C3)[C:4](=[O:12])/[C:3]/1=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(=O)OC(=O)C=C1.C[Al](Cl)Cl.CCCCCC>ClCCl>[CH3:1][CH:2]1[CH:10]=[CH:5][C:4](=[O:12])/[C:3]/1=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7923Maleic AnhydrideHCID 8058HexaneHCID 101908Methylaluminum dichlorideHCID 18436294HCID 18436294, compound

Product 1

HCID 58807382HCID 58807382, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, a solution of 3-methyl-2-[1-phenyl-meth-(E)-ylidene]-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one (5) (250 mg, 1 mmol., 1 eq.) and maleic anhydride (490 mg, 5 mol., 5 eq.) in dichloromethane (10 cm3) was treated with a 1.0 M solution of MeAlCl2 in hexane (1.1 cm3, 1.1 mmol., 1.1 eq.). This mixture was heated to reflux for 5 hours. Silica (ca. 2.5 g) was added and the solvent was removed under reduced pressure. Flash column chromatography (Hex-EtOAc; 3:1) gave 4-methyl-5-[1-phenyl-meth-(E)-ylidene]-cyclopent-2-enone (6) (compound CTC-150) (138 mg, 75%) as a colourless solid. Rf=0.5 (Hex-EtOAc; 3:1); δH (400 MHz, CDCl3) 1.22 (3H, d, J 7.0 Hz, CH3), 3.84-4.00 (1H, m, CH), 6.40 (1H, dd, J 1.75, 5.75 Hz, CH), 7.39-7.44 (4H, ArH), 7.54 (2H, d, J 7.0 Hz, AH, 7.60 (1H, ddd, J 1.0, 2.5, 5.75 Hz, CH); δC (100 MHz, CDCl3) 16.3, 38.8, 128.7, 129.3, 130.6, 131.7, 133.6, 134.8, 138.3, 163.9, 197.4; Found C, 84.66; H, 6.60%, C13H12O requires C, 84.78; H, 6.57%.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 5 hours
  3. additionSilica (ca. 2.5 g) was added
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-10f6293642c444b794d6d4095c2a5637
Source dataset
uspto-grants-2007_12
Patent number
US07304186B2

Reaction notes

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