Dimethylformamide → 4-(2-Methyl-2-propenyl)-1-indanone

HRID 1646616Notes

Reaction equation

HRID 1646616 reaction equation
[CH3:1][C:2](=[CH2:17])[CH2:3][Sn](CCCC)(CCCC)CCCC.Br[C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH2:21][CH2:22][C:23]2=[O:28].CN(C)C=O.[F-].[K+]>O.[Pd].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:3][C:2](=[CH2:1])[CH2:17][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH2:21][CH2:22][C:23]2=[O:28]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 987131-Indanone, 4-bromo-HCID 522689Potassium FluorideHCID 11013379Methallyltri-n-butyltin

Product 1

HCID 198011724-(2-Methyl-2-propenyl)-1-indanone

Reagents, catalysts & solvents 2

HCID 57646695Palladium;tetraphenyl-lambda5-phosphaneCatalystHCID 962WaterSolvent

Procedure

9 g of (2-methyl-2-propenyl)-tributyl stannane, 5.25 g of 4-bromo indanone, 50 ml of dimethylformamide and 300 g of tetrakis phenyl phosphine palladium are heated to 125° C. under agitation for 45 minutes. After cooling, the mixture is poured into an iced solution of 7.5 g of potassium fluoride in 300 ml of water, agitated for 5 minutes and filtered on celite. The filtrate is extracted with isopropyl ether, dried and concentrated to dryness under reduced pressure. The residue is chromatographed on silica, eluting with a hexane-ethyl acetate mixture (8-2) and 4 g of expected product is recovered.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered on celite
  3. extractionThe filtrate is extracted with isopropyl ether
  4. customdried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue is chromatographed on silica
  7. washeluting with a hexane-ethyl acetate mixture (8-2) and 4 g of expected product
  8. customis recovered

Sources & evidence

ORD record
ord-198b373b3b2a4876849e48783228bfb1
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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