Hexamethylphosphoramide → Ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-2-propylchromane-2-carboxylate

HRID 479633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479633
[CH2:1]([C:4]1[CH:29]=[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[O:18]2)=[CH:13][CH:12]=1)[CH2:2][CH3:3].CN(C)P(N(C)C)(N(C)C)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH2:59][CH2:60][CH3:61]>C1COCC1>[CH2:1]([C:4]1[CH:29]=[C:28]([O:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][C:17]([CH2:59][CH2:60][CH3:61])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[O:18]2)=[CH:13][CH:12]=1)[CH2:2][CH3:3]

Komponenten

6

Edukt 4

HCID 12679HexamethylphosphoramideHCID 336431-IodopropaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18772266Ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-chromane-2-carboxylate

Produkt 1

HCID 18772268Ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-2-propylchromane-2-carboxylateAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 2 ml THF solution of ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-chromane-2-carboxylate (Example 1, Step B) (100 mg, 0.204 mmol) were added hexamethylphosphoramide (0.046 ml, 0.26 mmol) and sodium bis(trimethylsilyl)amide (1.0M THF solution) (0.265 ml, 0.265 mmol) upon cooling in a dry ice-acetone bath. After stirring at that temperature for 30min, to it was added iodopropane (0.06 ml, 6.2 mmol). The cooling bath was removed and the reaction mixture was gradually warmed to rt overnight. The solvent was removed under reduced pressure, diluted with AcOEt and water. The organic layer was separated. The aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 5% AcOEt/hexanes gave the title compound as a clear oil 33 mg (30%).

Aufarbeitung

  1. temperatureupon cooling in a dry ice-acetone bath
  2. customThe cooling bath was removed
  3. customThe solvent was removed under reduced pressure
  4. additiondiluted with AcOEt and water
  5. customThe organic layer was separated
  6. extractionThe aqueous layer was extracted twice with AcOEt
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed on silica gel
  11. washElution with 5% AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-064633f716e8441997a81df662da6c89
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645997B2

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