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

HRID 1646616노트

반응식

HRID 1646616 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 57646695Palladium;tetraphenyl-lambda5-phosphane촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-198b373b3b2a4876849e48783228bfb1
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180741

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