Methyl 4-trimethylsilylethynylbenzoate → Methyl 4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

HRID 428213

Reaktionsgleichung

Reaktionsgleichung von HRID 428213
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](Cl)=[O:15])[CH:5]=[CH:4][C:3]1=2.C[Si]([C:22]#[C:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)(C)C.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[O:15]=[C:14]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)[C:22]#[C:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 640161Methyl 4-trimethylsilylethynylbenzoateHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 9799722Methyl 4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

8.4 g (36 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl chloride, 6.9 g (29.7 mmol) of methyl 4-trimethylsilylethynylbenzoate and 100 ml of dichloromethane are introduced into a round-bottomed flask. 16.8 g (125 mmol) of AlCl3 are added portionwise at 0° C. and the mixture is stirred at room temperature for 8 hours. The reaction medium is poured into ice and extracted with dichloromethane, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of dichloromethane and hexane (50/50% by volume). 6.8 g (61%) of the expected product are collected, with a melting point of 113-4° C.

Aufarbeitung

  1. additionThe reaction medium is poured into ice
  2. extractionextracted with dichloromethane
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of dichloromethane and hexane (50/50% by volume)
  9. custom6.8 g (61%) of the expected product are collected, with a melting point of 113-4° C.

Quellen und Nachweise

ORD-Eintrag
ord-e01264b5fb444276bc0a7c64dfa92a4d
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313162B1

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