Ammonium Chloride → HCID 66743816, Verbindung

HRID 1054133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054133
CC(C)([O-])C.[K+].COP([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])(OC)=O.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH:31]([F:33])[F:32])=[C:26]([CH:29]=1)[CH:27]=O.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH:31]([F:32])[F:33])=[C:26](/[CH:27]=[CH:13]/[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH:29]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 47709495-Chloro-2-(difluoromethoxy)benzaldehydHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 66743816HCID 66743816, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of potassium tert-butoxide (0.407 g, 3.63 mmol) in THF (10 mL) were added tert-butyl 2-(dimethoxyphosphoryl)acetate (0.528 mL, 2.66 mmol) and 5-chloro-2-(difluoromethoxy)benzaldehyde (0.50 g, 2.420 mmol) at 0° C. After 4 hrs, NH4Cl solution was added and the reaction mixture was diluted with EtOAc, washed with sat'd NH4Cl solution, sat'd NaHCO3, and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The crude product was purified by normal phase chromatography. Intermediate 15A was obtained as a white solid 550 mg (74%). MS (ESI) m/z: 327.0 (M+Na)+. 19F NMR (376 MHz, CDCl3) δ: −81.11 (1F, s) ppm.

Aufarbeitung

  1. washwashed with sat'd NH4Cl solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by normal phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d65edc9dd3bd4fec9197b7491be7af53
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394276B2

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