Tributylphosphine → Ethyl 3-(4-{[2-(benzyloxy)benzyl]oxy}-3,5-difluorophenyl)propanoate

HRID 1678599

Reaktionsgleichung

Reaktionsgleichung von HRID 1678599
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[F:19][C:20]1[CH:21]=[C:22]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:23]=[C:24]([F:27])[C:25]=1O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>CO.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][O:12][C:25]1[C:24]([F:27])=[CH:23][C:22]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:21][C:20]=1[F:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 3447842-(Benzyloxy)benzaldehydeHCID 4311764Sodium borohydrideHCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate

Produkt 1

HCID 23136287Ethyl 3-(4-{[2-(benzyloxy)benzyl]oxy}-3,5-difluorophenyl)propanoateAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-(Benzyloxy)benzaldehyde (274 mg, 1.3 mmol) dissolved in methanol (20 mL), sodium borohydride (73 mg, 1.9 mmol) was added thereto, and then the mixture was stirred with ice cooling for 2 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 mL). Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (200 mg, 0.86 mmol), tributylphosphine (0.23 mL, 1.1 mmol) and azodicarbonyldipiperidine (282 mg, 1.1 mmol) were added thereto, and the mixture was stirred at room temperature for 12 hours. The reaction solution was purified with alumina column chromatography (ethyl acetate) and silica gel column chromatography (hexane/ethyl acetate=100:0 to 80:20) to give the title compound (162 mg, yield 29%) as an oily matter.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in tetrahydrofuran (10 mL)
  5. stirringthe mixture was stirred at room temperature for 12 hours
  6. customThe reaction solution was purified with alumina column chromatography (ethyl acetate) and silica gel column chromatography (hexane/ethyl acetate=100:0 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-548ce631baac49c4bd2df2324448bc0a
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008525B2

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