tert-Butyl methyl ether → [3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde

HRID 253357ノート

反応式

HRID 253357 の反応式
C(O[CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])[CH2:6]1)C=C.I([O-])(=O)(=O)=O.[Na+].[C:32]([O:36]C)(C)(C)[CH3:33]>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:15]2[O:16][C:17]([CH3:18])=[C:13]([CH2:12][O:11][CH:7]3[CH2:8][CH2:9][CH2:10][CH:5]([CH2:33][CH:32]=[O:36])[CH2:6]3)[N:14]=2)=[CH:24][CH:23]=1

参加物

7

反応物 3

HCID 15413tert-Butyl methyl etherHCID 23667635Sodium periodateHCID 587633724-(3-Allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyloxazole

生成物 1

HCID 86594696[3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

2.0 g of 4-(3-allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyloxazole are dissolved in 50 ml of diethyl ether, and 3.8 g of sodium periodate, dissolved in 50 ml of water, are added. At 0° C., 1 ml of an osmium tetroxide solution (2.5% by weight in tert-butanol) is added, and the mixture is stirred vigorously at room temperature. After 8 h, 100 ml of methyl tert-butyl ether are added and the mixture is washed with a saturated sodium thiosulfate solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5). This gives 1.4 g of [3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]-acetaldehyde as a yellow-brown oil. C20H25NO4 (343.42), MS (ESI): 344 (M+H+), Rf (n-heptane:ethyl acetate=1:1)=0.25.

後処理

  1. additionare added
  2. washthe mixture is washed with a saturated sodium thiosulfate solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5)

出典と根拠

ORDレコード
ord-5acb7c2469424b8796dd5609621eb3f3
出典データセット
uspto-grants-2011_01
特許番号
US07872034B2

反応ノート

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