Acetic Acid → N-(3-phenoxyphenyl)[[3-(1,1-dimethylethoxy)phenyl]methyl]amine

HRID 1018229

Reaktionsgleichung

Reaktionsgleichung von HRID 1018229
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[O:14]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[O:14]([C:21]1[CH:22]=[C:23]([NH:24][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:7]=2)[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 771353-PhenoxyanilineHCID 5049666Sodium triacetoxyborohydrideHCID 157122243-Tert-butoxybenzaldehyde

Produkt 1

HCID 10936948N-(3-phenoxyphenyl)[[3-(1,1-dimethylethoxy)phenyl]methyl]amineAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

EX-654B) The 3-t-butoxybenzaldehyde (0.585 g, 3.27 mmol) product from EX-654A and 3-phenoxyaniline (0.595 g, 3.21 mmol) were combined in 50 mL of THF, then solid NaBH(OAc)3 (0.860 g, 4.06 mmol) was added, and the mixture was stirred until uniform. Acetic acid (0.2 g, 3.33 mmol) was added, and the mixture was stirred at room temperature for 4 h, then quenched with 5% aq. NaHCO3. The aqueous layer was separated and extracted twice with ether. The combined ether layers were washed with water and brine, dried over MgSO4, filtered, and evaporated to give 1.29 g (115%) of crude product as a brown oil. Chromatography on silica gel eluting with 0-10% ethyl acetate in hexane gave 464 mg (40%) of the desired N-(3-phenoxyphenyl)[[3-(1,1-dimethyl-ethoxy)phenyl]methyl]amine product as a colorless oil, pure by TLC. MS m/z=347 [M+].

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 4 h
  2. customquenched with 5% aq. NaHCO3
  3. customThe aqueous layer was separated
  4. extractionextracted twice with ether
  5. washThe combined ether layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give 1.29 g (115%) of crude product as a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-530ed20e65e9454e8d7fdff4c459861a
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479552B2

Verknüpfte Notizen

Wird geladen…