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 1676143ノート

反応式

HRID 1676143 の反応式
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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e10ea9ac67b347f28f9a449dc2d9bb4b
出典データセット
uspto-grants-2011_08
特許番号
US08003800B2

反応ノート

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