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

HRID 1646616ノート

反応式

HRID 1646616 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 57646695Palladium;tetraphenyl-lambda5-phosphane触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-198b373b3b2a4876849e48783228bfb1
出典データセット
uspto-grants-1993_01
特許番号
US05180741

反応ノート

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