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Water → HCID 19029781, Verbindung

HRID 2260167
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2260167
[H-].[Na+].[OH:3][C:4]1[CH:15]=[C:14]([O:16][CH2:17][C:18]([C:20]2[CH:29]=[CH:28][C:27]3[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=3[CH:21]=2)=[O:19])[CH:13]=[CH:12][C:5]=1[C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7].[CH3:34][O:35][CH2:36][CH2:37][O:38][CH2:39]Cl.O>CN(C=O)C>[CH3:34][O:35][CH2:36][CH2:37][O:38][CH2:39][O:3][C:4]1[CH:15]=[C:14]([O:16][CH2:17][C:18]([C:20]2[CH:29]=[CH:28][C:27]3[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=3[CH:21]=2)=[O:19])[CH:13]=[CH:12][C:5]=1[C:6]([O:8][CH2:9][C:10]1[CH:6]=[CH:5][CH:4]=[CH:15][CH:11]=1)=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 21474550HCID 21474550, Verbindung

Produkt 1

HCID 19029781HCID 19029781, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

1.65 g (55 mmol) of sodium hydride (80% in oil) and 50 ml of DMF are introduced into a flask. A solution of 23.6 g (50 mmol) of allyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl methoxy)benzoate in 200 ml of DMF is added dropwise and the mixture is stirred until evolution of gas has ceased. 6.3 ml (55 mmol) of 2-methoxy ethoxymethyl chloride are then added dropwise and the reaction mixture is stirred for 2 hours. It is poured into water and extracted with ethyl ether, and the organic phase is separated, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column, eluted with a mixture of dichloromethane/ethyl ether (98:2). After evaporation of the solvents, 19.2 g (69%) of the expected ester are collected in the form of a slightly yellow oil.

Aufarbeitung

  1. stirringthe reaction mixture is stirred for 2 hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane/ethyl ether (98:2)
  9. customAfter evaporation of the solvents, 19.2 g (69%) of the expected ester
  10. customare collected in the form of a slightly yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-eaae29a9ffff48dd83891a7b3d6b8970
Quelldatensatz
uspto-grants-1995_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05476860

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