Ethyl diazoacetate → Ethyl 1,3-dimethyl-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate

HRID 1027907

Reaktionsgleichung

Reaktionsgleichung von HRID 1027907
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].F[B-](F)(F)F.C([O+](CC)CC)C.[N+](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N-].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH3:1][C:2]1[C:3]2[CH2:4][CH2:5][CH2:6][CH:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:7](=[O:13])[C:8]=2[CH:9]=[C:10]([CH3:12])[CH:11]=1

Komponenten

7

Edukt 4

HCID 12192Ethyl diazoacetateHCID 836193,4-dihydro-5,7-dimethylnaphthalen-1(2H)-oneHCID 516892Sodium BicarbonateHCID 2723982Triethyloxonium tetrafluoroborate

Produkt 1

HCID 69225430Ethyl 1,3-dimethyl-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one (1 g, 5.74 mmol) in anhydrous CH2Cl2 (20 mL) under nitrogen atmosphere was cooled to 0° C. To this solution was added triethyloxonium tetrafluoroborate (1M in CH2Cl2, 23 mL, 23 mmol), followed with ethyl diazoacetate (1.2 mL, 11.5 mmol). The mixture was stirred at ambient temperature for 16 hrs. The reaction was worked up with saturated sodium bicarbonate, diluted with water and CH2Cl2, and the layers were separated. The organic layer was dried with MgSO4, concentrated and the residue was purified by chromatography on silica gel eluting with 10% EtOAc/Hexanes to provide the title compound. 1H NMR (CD3OD) δ 1.29 (t, 3H), 1.97-2.12 (m, 4H), 2.28-2.30 (m, 3H), 2.30-2.31 (m, 3H), 2.59 (t, 2H), 4.28 (q, 2H), 6.86-6.90 (m, 1H), 6.95-6.99 (m, 1H), 13.17-13.22 (m, 1H). MS (M+H)+ m/z 261.

Aufarbeitung

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel eluting with 10% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-333643b3f30840b5ad90e20e859667a2
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735411B2

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