Water ethylacetate → 5-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

HRID 1962986ノート

反応式

HRID 1962986 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:16][O:17][C:18]=2/[CH:19]=C/C2C=CC=CC=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:35].[Na+].C(OCC)(=O)C.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[N:16][O:17][C:18]=2[CH:19]=[O:35])=[CH:8][N:7]=1)=[O:5])[CH3:2]

参加物

8

反応物 3

HCID 22728543Water ethylacetateHCID 23667635Sodium periodateHCID 666444395-[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

生成物 1

HCID 866472865-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester収率 72%

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-[3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (2.0 g, 4.5 mmol), osmium(VIII) oxide (28.6 mg, 0.11 mmol), sodium metaperiodate (3.85 g, 18 mmol), benzyltriethylammonium chloride (418 mg, 1.8 mmol) in dioxane (30 mL) and water (10 mL) was irradiated in the microwave for 15 min at 120° C. Extractive workup (ethyl acetate/water) was followed by drying of the organic phase over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) afforded the title compound (1.2 g, 72%) as a colourless gum. MS: m/e=371.1 [M+H]+.

後処理

  1. customwas irradiated in the microwave for 15 min at 120° C
  2. dry with materialby drying of the organic phase over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1)

出典と根拠

ORDレコード
ord-52e6c413ae234b8ba4622675bb79422a
出典データセット
uspto-grants-2013_04
特許番号
US08415379B2

反応ノート

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