1,2-Dibromoethane → 2,3-Dihydro-1,4-benzoxathiin-6-ol

HRID 398087

Reaktionsgleichung

Reaktionsgleichung von HRID 398087
Br[CH2:2][CH2:3]Br.C([O-])([O-])=O.[K+].[K+].[SH:11][C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=1[OH:19]>CC(C)=O>[O:19]1[C:13]2[CH:14]=[CH:15][C:16]([OH:18])=[CH:17][C:12]=2[S:11][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27361672-Mercaptobenzene-1,4-diol

Produkt 1

HCID 125159102,3-Dihydro-1,4-benzoxathiin-6-olAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

1,2-Dibromoethane (2.3 mL, 26.7 mmol) and K2CO3 (8.21 g, 59.4 mmol) were slurried in acetone (250 mL) and a solution of 2-sulfanyl-1,4-benzenediol (prepared according to J. Org. Chem. 1990, 55, 2736) (4.22 g, 29.7 mmol) in acetone (50 mL) was added over 4 h to the stirred mixture. Once the addition was complete stirring was continued for a further 10 h before the solvent was removed in vacuo. The residue was partitioned between water (50 mL) and EtOAc (50 mL), the aqueous layer was extracted with EtOAc (50 mL) and the combined organic layers were dried (MgSO4) and evaporated. Purification of the residue by column chromatography [SiO2; 9:1 (pentane/EtOAc)] gave the title compound (2.48 g, 55%) as a pale orange oil; δH (CDCl3, 400 MHz) 3.08 (2H, m), 4.31 (2H, m), 4.44 (1H, s), 6.42 (1H, d), 6.49 (1H, s), 6.66 (1H, d); MS m/z (ES−) 167 (M−H+).

Aufarbeitung

  1. additionOnce the addition
  2. customwas removed in vacuo
  3. customThe residue was partitioned between water (50 mL) and EtOAc (50 mL)
  4. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. customevaporated
  7. customPurification of the residue by column chromatography [SiO2; 9:1 (pentane/EtOAc)]

Quellen und Nachweise

ORD-Eintrag
ord-f0178ef1a2d64aa7aa47d483c92b2062
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610747B2

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