Water → HCID 6991727, Verbindung

HRID 2413200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2413200
[CH3:1][C:2]1([CH3:11])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:4]([CH2:9][OH:10])[O:3]1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1COCC1>[C:15]1([CH2:14][O:8][CH2:7][C@@H:5]2[C@@H:4]([CH2:9][O:10][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:3][C:2]([CH3:11])([CH3:1])[O:6]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 785244(-)-2,3-O-Isopropylidene-D-threitol

Produkt 1

HCID 6991727HCID 6991727, VerbindungAusbeute 120,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of (4R-trans)-(-)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (51 g) in THF (400 ml) was added dropwise to a stirred suspension of sodium hydride (17.5 g of 80% in oil) in THF (200 ml). After 0.75 h, benzyl bromide (116.3 g) was added dropwise and the resulting mixture was stirred for 18 h, and was then heated at reflux for 2 h. After stirring for a further 20 h at 20°, the mixture was cooled in ice, water (10 ml) was added and the mixture was evaporated to dryness. The residue was extracted with ER, and the organic solution was dried and the solvent was evaporated giving a crude product (130 g) which was used without further purification.

Aufarbeitung

  1. temperaturewas then heated
  2. temperatureat reflux for 2 h
  3. stirringAfter stirring for a further 20 h at 20°
  4. temperaturethe mixture was cooled in ice
  5. customthe mixture was evaporated to dryness
  6. extractionThe residue was extracted with ER
  7. customthe organic solution was dried
  8. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f58bc6b713b54d53ac066533d4079a27
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04496579

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