Tetrahydrofuran → 3-Cyclopropyl-2-propenoic acid ethyl ester

HRID 626442ノート

反応式

HRID 626442 の反応式
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]1[CH2:21]O[CH2:19][CH2:18]1.C1(C=O)CC1>CN(C=O)C.O>[CH:17]1([CH:21]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:19][CH2:18]1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 123114Cyclopropanecarboxaldehyde

生成物 1

HCID 534018523-Cyclopropyl-2-propenoic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

At 0° C., 13.0 ml (64.85 mmol) of ethyl diethylphosphonoacetate were added dropwise to a suspension of 2.59 g (64.85 mmol) of sodium hydride (60% in mineral oil) in 110 ml of abs. THF. After 30 min, the mixture was warmed to RT and, after cooling again to 0° C., 5.3 ml (71.34 mmol) of cyclopropanecarboxaldehyde were added dropwise. After the end of the addition, the reaction mixture was warmed to RT and diluted with 35 ml of DMF. The mixture was stirred at RT overnight and then added to water. The mixture was extracted three times with ethyl acetate. The combined organic phases were concentrated under reduced pressure and the crude product was purified by filtration through silica gel (mobile phase cyclohexane/ethyl acetate 10:1→6:1). This gave 8.53 g of the target product (93.8% of theory).

後処理

  1. temperatureafter cooling again to 0° C.
  2. additionAfter the end of the addition
  3. temperaturethe reaction mixture was warmed to RT
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. concentrationThe combined organic phases were concentrated under reduced pressure
  6. filtrationthe crude product was purified by filtration through silica gel (mobile phase cyclohexane/ethyl acetate 10:1→6:1)

出典と根拠

ORDレコード
ord-629f24e922994f8a9e8f0bc6ae0776f1
出典データセット
uspto-grants-2016_04
特許番号
US09309198B2

反応ノート

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