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

HRID 1901362
Notes
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Reaction equation

HRID 1901362 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8c3fd0c2c26e4eb297c93d952efee467
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05576343

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes