Ammonium Chloride → 3-(Pyrid-3-yl)-4-(2-chlorophenyl)but-1-ene-3,4-diol

HRID 1613641Notes

Reaction equation

HRID 1613641 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[O:17])[CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[OH:9])[CH:2]=1.[CH:18]([Mg]Br)=[CH2:19].[Cl-].[NH4+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:17])([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[OH:9])[CH:18]=[CH2:19])[CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 197742061-(Pyrid-3-yl)-2-(2-chlorophenyl)-2-hydroxyethanoneHCID 178418507HCID 178418507, compound

Product 1

HCID 197741953-(Pyrid-3-yl)-4-(2-chlorophenyl)but-1-ene-3,4-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13 g (0.0531 mol) of 1-(pyrid-3-yl)-2-(2-chlorophenyl)-2-hydroxyethanone in tetrahydrofuran (THF) was added dropwise to a freshly prepared solution of 0.18 mol of vinylmagnesium bromide in 80 ml of THF at room temperature. Stirring was carried out for three hours at room temperature, after which the solution was hydrolyzed by adding ammonium chloride solution. The aqueous phase was extracted twice with ethyl acetate. The collected organic phases were dried over Na2SO4 and then filtered, and the filtrate was evaporated down. The crude product was stirred with methyl tert-butyl ether, filtered off under suction and dried to give a product of melting point 110°-112° C.

Workup

  1. extractionThe aqueous phase was extracted twice with ethyl acetate
  2. dry with materialThe collected organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated down
  5. stirringThe crude product was stirred with methyl tert-butyl ether
  6. filtrationfiltered off under suction
  7. customdried
  8. customto give a product of melting point 110°-112° C.

Sources & evidence

ORD record
ord-4c88a53071ba4dd6acd70af697b24b59
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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