Acetonitrile → HCID 86628605, compound

HRID 658970Notes

Reaction equation

HRID 658970 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][S+]2CCCC2)[CH:9]=1.[Cl:20][C:21]1[CH:22]=[C:23]([C:28]2[C:29]([CH:34]=[O:35])=[CH:30][CH:31]=[CH:32]C=2)[CH:24]=[C:25]([Cl:27])[CH:26]=1.[OH-].[K+].CC#[N:40]>>[Cl:20][C:21]1[CH:22]=[C:23]([C:28]2[C:29]([CH:34]3[CH:14]([C:10]4[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=4)[O:35]3)=[CH:30][CH:31]=[CH:32][N:40]=2)[CH:24]=[C:25]([Cl:27])[CH:26]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 114024753′,5′-Dichloro[1,1′-biphenyl]-2-carboxaldehydeHCID 86628606HCID 86628606, compound

Product 1

HCID 86628605HCID 86628605, compound

Procedure

To a suspension of 1-(pyridin-3-ylmethyl)tetrahydrothiophenium hexafluorophosphate (4.97 g, prepared according to JACS, 1997 (119), 12376) and 3′,5′-dichlorobiphenyl-2-carbaldehyde (3.07 g) in 80 mL of MeCN was added aqueous KOH (2 M, 12.18 mL). The reaction was stirred at room temperature for 21 h, then partitioned between water and dichloromethane. The aqueous solution was extracted with dichloromethane (4×). The combined organic solutions were dried over Na2SO4 and concentrated. Flash chromatography (10% to 80% EA in hexanes) provided 2.86 g of 2-(3,5-dichlorophenyl)-3-(3-pyridin-3-yloxiran-2-yl)pyridine 1-1 as a white solid.

Workup

  1. custompartitioned between water and dichloromethane
  2. extractionThe aqueous solution was extracted with dichloromethane (4×)
  3. dry with materialThe combined organic solutions were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-afa1997d627149ecabbb984b6782a102
Source dataset
uspto-grants-2011_12
Patent number
US08080543B2

Reaction notes

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