Hydrochloric Acid → 4-(4-Fluorophenyl)but-3-enoic acid

HRID 974997ノート

反応式

HRID 974997 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Cl-].[C:11]([CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:13])=[O:12].CC(C)([O-])C.[K+].[H][H].Cl>O1CCCC1.O.CCOCC>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:15]/[CH2:14][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 680234-FluorobenzaldehydeHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 103973854-(4-Fluorophenyl)but-3-enoic acid収率 50%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

74.4 g of 4-fluorobenzaldehyde and 233.6 g of β-carboxyethyl-triphenyl phosphonium chloride were suspended in 700 ml of tetrahydrofuran and these were incubated on ice and stirred. Into this 500 ml tetrahydrofuran solution of 141.4 g of potassium tert-butoxide was added slowly dropwise. 30 minutes after temperature was brought to room temperature and then they were stirred for 10 hours. After adding thereto ice water and cleaning with ether, the hydrogen-ion concentration of water layer was set to pH2 with undiluted hydrochloric acid. Extraction was then made with ethyl acetate. After drying with magnesium sulfate and concentration made under reduced pressure, the solid obtained was recrystallized from hydrous ethanol, and 53.98 g of marked compound (yield: 50%) was obtained as white needle crystal.

後処理

  1. custom30 minutes
  2. customwas brought to room temperature
  3. stirringthey were stirred for 10 hours
  4. additionAfter adding
  5. extractionExtraction
  6. dry with materialAfter drying with magnesium sulfate and concentration
  7. customthe solid obtained
  8. customwas recrystallized from hydrous ethanol

出典と根拠

ORDレコード
ord-1ed36f677c7944f586fef193ca317de3
出典データセット
uspto-grants-1997_03
特許番号
US05607953

反応ノート

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