Imidazole → 2-[5-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-2-thienyl]acetic acid

HRID 2279959ノート

反応式

HRID 2279959 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[S:8][C:7]([CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1>[Si:18]([O:1][CH2:2][CH2:3][C:4]1[S:8][C:7]([CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

参加物

8

反応物 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 579889872-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid

生成物 1

HCID 1236351082-[5-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-2-thienyl]acetic acid収率 23%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-[5-(2-hydroxyethyl)-2-thienyl]acetic acid (1.35 g, 7.26 mmol) and imidazole (1.04 g, 15.25) in N,N-dimethylformamide (18 mL) was added tert-butyldimethylsilyl chloride (2.29 g, 15.25 mmol) over 20 minutes. The resultant solution was stirred at room temperature for one hour. Tetrahydrofuran (18 mL) was then added and reaction solution cooled to 0° C. A solution of potassium carbonate (1.04 g, 7.6 mmol) in water (18 mL) was added and the solution stirred for 20 minutes. The reaction solution was then partitioned between ethyl acetate and brine. The organic phases were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 0-50% ethyl acetate in iso-hexane to give the title compound as a yellow oil (500 mg, 23%).

後処理

  1. customreaction solution
  2. customThe reaction solution was then partitioned between ethyl acetate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0-50% ethyl acetate in iso-hexane

出典と根拠

ORDレコード
ord-25722c27ca444afea69d06427a5365e9
出典データセット
uspto-grants-2015_09
特許番号
US09133185B2

反応ノート

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