Sodium Hydroxide → (R)-5-tert-butoxy-2-isopropoxy-7-oxiranyl-benzothiazole

HRID 1426879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426879
[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@@H:19]([OH:22])[CH2:20]Cl)[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[N:11][C:10]=2[CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CC(OC)(C)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@@H:19]2[CH2:20][O:22]2)[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[N:11][C:10]=2[CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 86696599(R)-1-(5-tert-Butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanol

Produkt 1

HCID 86696600(R)-5-tert-butoxy-2-isopropoxy-7-oxiranyl-benzothiazoleAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 15413tert-Butyl methyl etherLösungsmittel2×

Versuchsvorschrift

To a solution of (R)-1-(5-tert-butoxy-2-isopropoxybenzo[d]thiazol-7-yl)-2-chloro-ethanol (140 g, 407.1 mmol) in TBME (420 ml) was added dropwise NaOH aqueous solution (2M, 420 ml) followed by tetrabutylammonium iodide (7.52 g, 20.36 mmol) added in one portion. After 4 h at 26° C., 400 ml TBME was added and the organic layer was separated. The aqueous layer was extracted with TBME (400 ml). The combined organic layers were washed with water (400 ml) and brine (400 ml) to give (R)-5-tert-butoxy-2-isopropoxy-7-oxiranyl-benzothiazole (122 g).

Aufarbeitung

  1. additionadded in one portion
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with TBME (400 ml)
  4. washThe combined organic layers were washed with water (400 ml) and brine (400 ml)

Quellen und Nachweise

ORD-Eintrag
ord-74fd751939b04858992343eca6cbc05e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933108B2

Notizen zur Reaktion

Wird geladen…