Hydrochloric Acid → 1-[N-ethyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

HRID 1741418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741418
[C:1]([N:4]([CH:23]1[C:31]2[C:26](=[C:27]([O:32][CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:5][C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)(=O)[CH3:2].Cl>C1COCC1>[CH2:1]([N:4]([CH:23]1[C:31]2[C:26](=[C:27]([O:32][CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:5][C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:10]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 183674301-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

Produkt 1

HCID 183672641-[N-ethyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indeneAusbeute 121,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.40 g) in THF (10 ml) was added 1M solution of borane-THF complex in THF (9 ml) at room temperature. The reaction mixture was refluxed for 8 hours and cooled down to room temperature. 1N aqueous HCl solution (25 ml) was added to the reaction mixture. After being stirred for 1 hour at room temperature, the mixture was partitioned between ethyl acetate and 1N aqueous NaOH solution. The organic layer was washed with brine. The dried solvent was evaporated in vacuo to give 1-[N-ethyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.47 g). MS (m/z): 425 (M+ +1) NMR (CDCl3, δ): 7.66-7.58 (4H, m), 7.39-7.08 (8H, m), 6.70 (1H, d, J=7.7 Hz), 4.67 (1H, t, J=7.6 Hz), 3.81 (3H, s), 3.18-2.80 (2H, m), 2.73 (2H, q, J=7.2 Hz), 2.35-1.84 (2H, m), 1.14 (3H, t, J=7.2 Hz)

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. customthe mixture was partitioned between ethyl acetate and 1N aqueous NaOH solution
  3. washThe organic layer was washed with brine
  4. customThe dried solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11f001be355f42fb9847c27b06070a17
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972965

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