Potassium Carbonate → 3-(1-Adamantyl)-4-methoxyphenylacetylene

HRID 710359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710359
[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH:14]=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:21]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]12([C:11]3[CH:12]=[C:13]([C:14]#[CH:21])[CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 540295304-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Produkt 1

HCID 152893643-(1-Adamantyl)-4-methoxyphenylacetyleneAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-(1-admantanyl)-4-methoxybenzaldehyde (0.12 g, 0.42 mmol), dimethyl(1-diazo-2-oxopropyl)phosphonate (0.097 g, 0.51 mmol) and K2CO3 (0.069 g, 0.5 mmol) in anhydrous MeOH (5 ml) was stirred overnight at 80° C. The solvent was evaporated and the residue was diluted to 50 ml with EtOAc, washed with H2O, dried over MgSO4 and filtered. The filtrate was passed through SiO2 bead and the filtrate was evaporated to dryness to give the title product (0.05 g; 42%), which was used for the next step without purification. 1H-NMR (CDCl3) 1.75 (s, 3H); 2.05 (broad s, 9H); 2.96 (s, 1H); 3.82 (s, 3H); 6.77 (d, 1H, J=8.31 Hz); 7.29-7.34 (m, 2H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-583b2cbe0e25486ab26c343936270957
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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