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Acetylacetone → 3-(7-Methoxy-6-methyl-indan-4-ylmethyl)-pentane-2,4-dione

HRID 1099360
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HRID 1099360 반응식
[CH3:1][O:2][C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([CH:12]=O)=[CH:5][C:4]=1[CH3:14].[C:15]([CH2:18][C:19](=[O:21])[CH3:20])(=[O:17])[CH3:16].[H][H]>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH2:12][CH:18]([C:19](=[O:21])[CH3:20])[C:15](=[O:17])[CH3:16])=[C:7]2[C:11]=1[CH2:10][CH2:9][CH2:8]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 3

HCID 31261AcetylacetoneHCID 771748277-Methoxy-6-methyl-indan-4-carbaldehydeHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 668129973-(7-Methoxy-6-methyl-indan-4-ylmethyl)-pentane-2,4-dione수율 25.2%

시약·촉매·용매 5

HCID 23938Palladium촉매HCID 176
Acetic Acid
용매
HCID 887Methanol용매
HCID 1140Toluene용매
HCID 8082Piperidine용매

실험 절차

To the solution of 7-Methoxy-6-methyl-indan-4-carbaldehyde (8.0 gm 0.042 mole) and Acetyl acetone (4.63 gm, 0.046 mole) in Toluene (80 ml), Piperidine (0.5 ml) and Acetic acid (0.5 ml) were added. The reaction mixture was refluxed over 3A° molecular sieve using dean stark apparatus for 24 hours. Toluene was distilled under vacuum to give a crude product, which was purified by column chromatography using 5% Ethyl acetate in Hexane. The fractions were distilled to give 3.0 gm of condensed product It was dissolved in Methanol (60 ml) and hydrogenation was carried out over 5% w/w Palladium on Barium sulphate (350 mg) at 40-50 psi. using Hydrogen gas at 25-30° C. The reaction mixture was filtered through hyflow bed and distilled under vacuum to give a 2.9 gm of desired compound as a viscous oil.

후처리

  1. temperatureThe reaction mixture was refluxed over 3A° molecular sieve
  2. customfor 24 hours
  3. distillationToluene was distilled under vacuum
  4. customto give a crude product, which
  5. customwas purified by column chromatography
  6. distillationThe fractions were distilled
  7. customto give
  8. custom3.0 gm of condensed product It
  9. customat 25-30° C
  10. filtrationThe reaction mixture was filtered through hyflow bed
  11. distillationdistilled under vacuum

출처 및 근거

ORD 기록
ord-0d836387610f4da99f1bf837610a4755
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143424B2

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