Hydrochloric Acid → Methyl 2-tert-butoxycarbonyl-1-chloro-1-cyclopropanecarboxylate

HRID 1956826ノート

反応式

HRID 1956826 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH:4]=[CH2:5].[Cl:12][CH:13](Cl)[C:14]([O:16][CH3:17])=[O:15].Cl>CN(C)C=O.O>[C:8]([O:7][C:3]([CH:4]1[CH2:5][C:13]1([Cl:12])[C:14]([O:16][CH3:17])=[O:15])=[O:6])([CH3:11])([CH3:10])[CH3:9]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8315Methyl dichloroacetateHCID 15458tert-Butyl acrylateHCID 24758Sodium hydride

生成物 1

HCID 10014285Methyl 2-tert-butoxycarbonyl-1-chloro-1-cyclopropanecarboxylate収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
10 °C

実験手順

80 g of 60% sodium hydride was suspended in 1,000 ml of N,N-dimethylformamide. To this suspension was dropped 352 ml of tert-butyl acrylate within 30 minutes under ice-cooling. Then 207 ml of methyl dichloroacetate was dropped into this reaction mixture within 1.5 hours while maintaining the internal temperature at 10° C. After the completion of the addition, the mixture was stirred for 2 hours while maintaining the internal temperature at 10° to 20° C. Then the reaction mixture was neutralized by adding concentrated hydrochloric acid and water was-further added thereto. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride. The extract was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The obtained residue was distilled under reduced pressure to thereby give 384 g (yield 84%) of methyl 2-tert-butoxycarbonyl-1-chloro-1-cyclopropanecarboxylate in the form of a colorless oily product.

後処理

  1. temperaturecooling
  2. additionAfter the completion of the addition
  3. temperaturewhile maintaining the internal temperature at 10° to 20° C
  4. additionwas-further added
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. distillationThe obtained residue was distilled under reduced pressure

出典と根拠

ORDレコード
ord-acfe2c0dd7c04502ac76248e379b1f73
出典データセット
uspto-grants-1998_07
特許番号
US05780669

反応ノート

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