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 1676143Notes

Reaction equation

HRID 1676143 reaction equation
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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e10ea9ac67b347f28f9a449dc2d9bb4b
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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