Water → HCID 86754162, Verbindung

HRID 580981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580981
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1)[CH:4]=[CH2:5].C[O:16][C:17](=[O:20])[CH2:18]Cl.O>CN(C=O)C>[C:17]([O:20][O:12][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([O:6][CH2:3][CH:4]=[CH2:5])=[CH:8][CH:9]=1)(=[O:16])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7295Methyl chloroacetateHCID 24758Sodium hydrideHCID 11744970(4-(Prop-2-en-1-yloxy)phenyl)methanol

Produkt 1

HCID 86754162HCID 86754162, VerbindungAusbeute 38,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (1.20 g; 60% dispersion in oil) was added over a period of 10 minutes to a stirred solution of 4-allyloxybenzyl alcohol (4.60 g) in DHF (20 ml) at 0° C. under an atmosphere of argon. After 0.5 hours, a solution of methylchloroacetate (3.30 g) in DMF (10 ml) was added over a period of 0.25 hours. The reaction mixture was stirred for 40 hours at ambient temperature. Water (300 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts were combined, washed with brine (2×100 ml), dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel using a 9:1 (v/v) mixture of hexane/ethyl acetate to give 4-allyloxyphenylmethyloxy acetate (2.42 g) as a colourless oil; NMR(CDCl3): 3.75(3H,s), 4.07(2H,s), 4.52(4H,m), 5.36(2H,m), 6.10(1H,m), 6.88(2H,m) and 7.28(2H,m); m/z 236(H).

Aufarbeitung

  1. extractionthe mixture extracted with ethyl acetate (3×100 ml)
  2. washwashed with brine (2×100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel using
  6. additiona 9:1 (v/v) mixture of hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-aa7a3fa4f1004114a4fed55e8f77e892
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919793

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