Ethanol → 2-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid

HRID 470964ノート

反応式

HRID 470964 の反応式
[Si]([O:8][CH2:9][CH2:10][C:11]1[S:15][C:14](CC#N)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[OH-:19].[K+].[CH2:21]([OH:23])[CH3:22]>O>[OH:23][CH2:21][CH2:22][C:14]1[S:15][C:11]([CH2:10][C:9]([OH:8])=[O:19])=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 579893012-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetonitrile

生成物 1

HCID 579889872-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A solution of 2-(5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetonitrile (example 4, step d) (3 g) in ethanol (30 mL) was added to a stirred solution of potassium hydroxide (1.20 g) in water (30 mL). The resulting mixture was stirred at 100° C. for 4 hours. The reaction was concentrated in vacuo and the resulting mixture was partitioned between brine and ethyl acetate. The aqueous layer was cooled with ice, acidified by dropwise addition of concentrated hydrochloric acid and extracted with yl acetate three times. The combined organic solutions were washed with brine, dried over sodium sulphate, filtered and the solvent evaporated in vacuo to give the subtitled compound as a yellow solid. Yield 1.75 g.

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resulting mixture was partitioned between brine and ethyl acetate
  3. temperatureThe aqueous layer was cooled with ice
  4. additionacidified by dropwise addition of concentrated hydrochloric acid
  5. extractionextracted with yl acetate three times
  6. washThe combined organic solutions were washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-b809be263bd04f12b560e92bfc9f832a
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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