tert-Butanol → 3-{4-[5-(4-Isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol

HRID 1676143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676143
C([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[O:13][C:14]([C:17]3[S:18][CH:19]=[C:20]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:21]=3[CH3:22])=[N:15][N:16]=2)=[CH:7][C:6]=1[CH3:27])C=C.C[N+]1([O-])CC[O:32]CC1.[C:36]([OH:40])([CH3:39])([CH3:38])C>CC(C)=O.O.O=[Os](=O)(=O)=O>[CH2:23]([C:20]1[C:21]([CH3:22])=[C:17]([C:14]2[O:13][C:12]([C:8]3[CH:9]=[C:10]([CH3:11])[C:5]([O:4][CH2:38][CH:36]([OH:40])[CH2:39][OH:32])=[C:6]([CH3:27])[CH:7]=3)=[N:16][N:15]=2)[S:18][CH:19]=1)[CH:24]([CH3:26])[CH3:25]

Komponenten

7

Edukt 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 673506622-(4-Allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazole

Produkt 1

HCID 237292443-{4-[5-(4-Isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazole (181 mg crude, 0.4 mmol) in a mixture of acetone and water (15:1.5 mL) are added N-methylmorpholine-N-oxide (250 mg, 1.85 mmol) and, subsequently, 2.5% OsO4 in tert.-butanol (0.1 mL). The mixture is stirred at rt for 36 h. The mixture is quenched into diethyl ether (75 mL) and washed with 1M aq. NaOH (50 mL), 1M aq. HCl (30 mL) and brine (20 mL). The organic phase is dried (Na2SO4), filtered and evaporated. The residue is purified by TLC (SiO2, EA-heptane) to give 118 mg of 3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol as a white powder; LC-MS: tR=1.00 min, [M+1]+=417.28; 1H NMR (D6-DMSO): δ, 7.70 (s, 2 H) 7.51 (s, 1 H), 4.96 (d, J=5.0 Hz, 1 H), 4.63 (t, J=5.6 Hz, 1 H), 3.68-3.89 (m, 3 H), 3.47 (t, J=5.6 Hz, 2 H), 2.51 (s, 3 H), 2.45 (m, 2 H), 2.33 (s, 6 H), 1.85 (m, 1 H), 0.90 (d, J=6.7 Hz, 6 H).

Aufarbeitung

  1. customThe mixture is quenched into diethyl ether (75 mL)
  2. washwashed with 1M aq. NaOH (50 mL), 1M aq. HCl (30 mL) and brine (20 mL)
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by TLC (SiO2, EA-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e10ea9ac67b347f28f9a449dc2d9bb4b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003800B2

Notizen zur Reaktion

Wird geladen…