Indole-3-Acetic Acid → Methyl indole-3-acetate

HRID 475494ノート

反応式

HRID 475494 の反応式
S(=O)(=O)(O)O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][C:16]([OH:18])=[O:17])=[CH:7]1.[OH-].[Na+].[CH3:21]O>O.C([O-])([O-])=O.[K+].[K+].CC(OC)(C)C>[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][C:16]([O:18][CH3:21])=[O:17])=[CH:7]1

参加物

8

反応物 4

HCID 802Indole-3-Acetic AcidHCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium Hydroxide

生成物 1

HCID 74706Methyl indole-3-acetate収率 81%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 11430Potassium Carbonate溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

Concentrated sulfuric acid (0.2 equiv.) was carefully added to a solution of 1H-indol-3-ylacetic acid in MeOH (1 M) and the reaction was stirred at rt for 2.5 h. The solution was cooled with an ice bath, and aqueous 2 N NaOH (0.18 equiv.) was slowly added such that T<10° C. The solution was diluted with water, and solid K2CO3 was then added until pH was neutral. The solution was extracted with MTBE (2×), washed with water (2×), brine, dried over Na2SO4, filtered, and concentrated to give a brown syrup. The crude syrup was dissolved in MTBE (1.4 mL/g) and transferred to a three necked flask fitted with a temperature probe, mechanical stirrer, addition funnel and nitrogen inlet. Hex was then slowly added to the stirring solution over 1 h. More Hex was then added over 2 h then left overnight. The suspension was filtered, washed with Hex, and dried on the fit under nitrogen for 20 h to give the title compound (81%) as a light orange solid.

後処理

  1. temperatureThe solution was cooled with an ice bath
  2. customwas slowly added such that T<10° C
  3. additionwas then added until pH
  4. extractionThe solution was extracted with MTBE (2×)
  5. washwashed with water (2×), brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown syrup
  10. customfitted with a temperature probe, mechanical stirrer, addition funnel and nitrogen inlet
  11. additionHex was then slowly added to the stirring solution over 1 h
  12. additionMore Hex was then added over 2 h
  13. waitthen left overnight
  14. filtrationThe suspension was filtered
  15. washwashed with Hex
  16. customdried on the fit under nitrogen for 20 h

出典と根拠

ORDレコード
ord-41c26aec9edf4605ba206389eaaf79aa
出典データセット
uspto-grants-2014_01
特許番号
US08637541B2

反応ノート

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