Water → 8-(2-Benzothiazolyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 857076

Reaktionsgleichung

Reaktionsgleichung von HRID 857076
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[O:17][CH2:16]1.O>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:21]1([OH:24])[CH2:22][CH2:23][C:18]2([O:25][CH2:15][CH2:16][O:17]2)[CH2:19][CH2:20]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7222BenzothiazoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Produkt 1

HCID 110875818-(2-Benzothiazolyl)-1,4-dioxaspiro[4.5]decan-8-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To benzothiazole (3.46 g, 25.6 mmol) dissolved in dry THF under a nitrogen atmosphere at −78° C. was added butyl lithium (17.1 mL of 1.5M solution, 1 equiv.) dropwise. The reaction mixture was stirred for 1 h then 1,4-cyclohexanedione mono-ethylene ketal dissolved in dry THF (15 mL) in one portion. The reaction mixture was stirred at −78° C. for a further 3 h then water (10 mL) was added. The mixture was warmed to room temperature and the white precipitate was collected on a filter, washed with water (2×20 mL) then dried under vacuum to give 4-(benzothiazol-2-yl)-1,1-ethylenedioxy-4-hydroxycyclohexane. The yield was 4.403 g (59%); mp 165° C.; 1H NMR (CDCl3) δ 8.05 (1H, m, benzothiazole H-4/7), 7.89 (1H, m, benzothiazole H-4/7), 7.47 (1H, m, benzothiazole H-5/6), 7.39 (1H, m, benzothiazole H-5/6), 4.02 (4H, s, ethylene 2×CH2), 3.16 (1H, s, OH), 2.41–2.31 (4H, m, cyclohexanone 2×CH2), 1.82–1.72 (4H, m, cyclohexanone 2×CH2); IR (KBr disc) 2897, 1501, 1437, 1368, 1038, 997, 764 cm−1; MS (AP+) 292 (M++1), 274 (M++1-H2O); Anal. (C15H17NO3) C, H, N.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at −78° C. for a further 3 h
  2. customthe white precipitate was collected on a filter
  3. washwashed with water (2×20 mL)
  4. customthen dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a2c330e36f5849ab9624cb0c9eb28174
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144893B2

Verknüpfte Notizen

Wird geladen…