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Water → Methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate

HRID 2371795
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2371795
[C-:1]#[N:2].[Na+].F[B-](F)(F)F.[CH3:9][O:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([N+]#N)[CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[C:15]([O:32][CH3:33])[CH:14]=1)=[O:12].C(OCC)(=O)C.O>CN(C)C=O>[C:1]([C:27]1[CH:28]=[C:29]2[C:24]([CH:23]=[CH:22][CH:21]=[C:20]2[CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:11]([O:10][CH3:9])=[O:12])=[CH:14][C:15]=2[O:32][CH3:33])=[CH:25][CH:26]=1)#[N:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 199063931-(4-Methoxycarbonyl-2-methoxyphenylmethyl)naphthalene-7-diazonium tetrafluoroborate

Produkt 1

HCID 19906375Methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of cuprous cyanide (2.52 g), sodium cyanide (1.68 g), and dimethylformamide (50 ml, distilled over CaH2) was stirred for 1 h. The homogeneous solution was cooled to 0° C. and a solution of 1-(4-methoxycarbonyl-2-methoxyphenylmethyl)naphthalene-7-diazonium tetrafluoroborate (2.62 g), in dimethylformamide (12 ml, distilled over CaH2) was added. The reaction was stirred for 15 min at 0° C. and then at room temperature for 16 h. The mixture was added to ethyl acetate (200 ml) and water (300 ml) and filtered through diatomaceous earth with ethyl acetate washes. The organic layer was washed (water, brine), dried (MgSO4), and evaporated. Flash chromatography of the residue, eluting with methylene chloride, and trituration of the product with hot ether afforded methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate (1.04 g, 56%) as a pale yellow solid; mp 138.5°-139.5° C.; MS(CI), m/e=33Z(M+H).

Aufarbeitung

  1. stirringThe reaction was stirred for 15 min at 0° C.
  2. waitat room temperature for 16 h
  3. filtrationfiltered through diatomaceous earth with ethyl acetate washes
  4. washThe organic layer was washed (water, brine)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. washFlash chromatography of the residue, eluting with methylene chloride, and trituration of the product with hot ether

Quellen und Nachweise

ORD-Eintrag
ord-d3e7d0cb01d04c7ea8922f446212c01c
Quelldatensatz
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05095038

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