Methanol → HCID 25128918, Verbindung

HRID 587944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587944
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH2:6][CH2:7][N:8]([CH3:31])[CH2:9][CH2:10][CH2:11][C:12]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)(C(OC)=O)[C:13]([O:15][CH3:16])=[O:14].CO.[H-].[Na+]>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH2:6][CH2:7][N:8]([CH3:31])[CH2:9][CH2:10][CH2:11][CH:12]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[C:13]([O:15][CH3:16])=[O:14]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 25128917HCID 25128917, Verbindung

Produkt 1

HCID 25128918HCID 25128918, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

To a solution of 0.349 g (0.694 mmol) of 3a in 20 mL of THF at 22° C. was added 0.281 mL (6.94 mmol) of methanol followed by 56 mg (1.39 mmol) of NaH (60% dispersion in mineral oil). The reaction was refluxed for 1 h, cooled to 22° C. and diluted with 100 mL of DCM. The mixture was washed with 50 mL of saturated NaHCO3, 50 mL of water, dried, and evaporated to give an oil. The oil was purified by flash chromatography on silica gel, eluting first with 2% methanol/DCM and then gradually increasing to 4% methanol/DCM to give 3b as a colorless oil; MS found M+H=446. The oxalate salt of 3r was recrystallized from ethyl acetate; mp 112-113.5° C.

Aufarbeitung

  1. temperatureThe reaction was refluxed for 1 h
  2. washThe mixture was washed with 50 mL of saturated NaHCO3, 50 mL of water
  3. customdried
  4. customevaporated
  5. customto give an oil
  6. customThe oil was purified by flash chromatography on silica gel
  7. washeluting first with 2% methanol/DCM
  8. temperaturegradually increasing to 4% methanol/DCM

Quellen und Nachweise

ORD-Eintrag
ord-6635e1b95ff04b5496d9222a5ebb4e2b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227918B2

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