Water → [3-(4-Formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester

HRID 2036274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036274
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.[C:14]([O:18][C:19](=[O:25])[NH:20][CH2:21][CH2:22][CH2:23]Br)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:14]([O:18][C:19](=[O:25])[NH:20][CH2:21][CH2:22][CH2:23][O:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 130742081-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-4-hydroxy-

Produkt 1

HCID 57828234[3-(4-Formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl esterAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Hydroxy-5,6,7,8-tetrahydro-naphthalene-1-carbaldehyde (109, 4.6 g, 29.1 mmol) (3-Bromopropyl)-carbamic acid tert-butyl ester (110, 4.6 g, 32 mmol), and potassium carbonate (6.03 g, 43.7 mmol) were stirred in 140 mL of dry DMF over night. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water and brine., dried with magnesium sulfate, filtered, concentrated and purified by flash chromatography (0-30% EtOAc/hexane) to give crude product, which was recrystallized from EtOAc/Hexane to give 5.8 g of 111, [3-(4-formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with material, dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-30% EtOAc/hexane)
  7. customto give crude product, which
  8. customwas recrystallized from EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-24cc1b6dd8064adb8115f637b2873f69
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575176B2

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