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Citric Acid → 2-[2-[4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]-3-hydroxyphenyl]vinyl]-5-benzofurancarbonitrile

HRID 53995
ノート
印刷プレビュー

反応式

HRID 53995 の反応式
C([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][C@H:14]1[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15]1)[CH:8]=O)(=O)C.[Cl-].[C:23]([C:25]1[CH:26]=[CH:27][C:28]2[O:32][C:31]([CH2:33][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:30][C:29]=2[CH:53]=1)#[N:24].C1CCN2C(=NCCC2)CC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(O)C.O>[C:19]([N:16]1[CH2:17][CH2:18][C@H:14]([O:13][C:12]2[CH:11]=[CH:10][C:7]([CH:8]=[CH:33][C:31]3[O:32][C:28]4[CH:27]=[CH:26][C:25]([C:23]#[N:24])=[CH:53][C:29]=4[CH:30]=3)=[CH:6][C:5]=2[OH:4])[CH2:15]1)(=[O:21])[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 311Citric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2 回HCID 21844326(5-Cyano-2-benzofuranyl)methyltriphenylphosphonium chlorideHCID 571530353-acetyloxy-4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]benzaldehyde

生成物 1

HCID 570808862-[2-[4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]-3-hydroxyphenyl]vinyl]-5-benzofurancarbonitrile収率 103.8%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1.3 g of 3-acetyloxy-4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]benzaldehyde and 2.22 g of (5-cyano-2-benzofuranyl)methyltriphenylphosphonium chloride were dissolved in a solvent mixture of 10 ml of tetrahydrofuran and 10 ml of ethanol, followed by the addition of 0.943 g of 1,8-diazabicyclo[5.4.0]-7-undecene and by subsequent stirring at room temperature for 2 hours. To the mixture obtained were further added 1.88 g of 1,8-diazabicyclo[5.4.0]-7-undecene and 3 ml of water, followed by stirring at room temperature for 2 hours. The thus prepared reaction solution was adjusted to pH 4-5 with 10% citric acid aqueous solution and concentrated under a reduced pressure, and the resulting residue was extracted with chloroform, and then dried. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a chloroform/ethanol mixture as an elution solvent, thereby obtaining 1.8 g of 2-[2-[4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]-3-hydroxyphenyl]vinyl]-5-benzofurancarbonitrile as a powdery mixture of E and Z forms.

後処理

  1. customTo the mixture obtained
  2. stirringby stirring at room temperature for 2 hours
  3. customThe thus prepared reaction solution
  4. concentrationconcentrated under a reduced pressure
  5. extractionthe resulting residue was extracted with chloroform
  6. customdried
  7. distillationAfter distilling off the solvent
  8. customthe resulting residue was purified

出典と根拠

ORDレコード
ord-2cff88edc8c34de8b5a1a53c8fb63c29
出典データセット
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05620991

反応ノート

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