Ammonium Chloride → HCID 15661752, compound

HRID 977584Notes

Reaction equation

HRID 977584 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:11][C:12]1[N:17]=[C:16](/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[CH:22]=[O:23])[CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C(OCC)C>[Br:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16](/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[CH:22]([OH:23])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[N:17]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15661750HCID 15661750, compoundHCID 178443577HCID 178443577, compound

Product 1

HCID 15661752HCID 15661752, compoundYield 196.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of octylmagnesium bromide (produced from 150 mg of magnesium in 5 ml of diethyl ether and 1.14 g of octyl bromide in 2.5 ml of diethyl ether) is instilled in a solution of 1.17 g of 5-(6-bromo-2-pyridyl)-(E,E)-2,4-pentadienaldehyde in 25 ml of diethyl ether with stirring and under argon atmosphere at -20° C. After 1.5 hours at -20° C., the reaction mixture is mixed with 15 ml of saturated ammonium chloride solution, shaken out with diethyl ether, dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/ethyl acetate=95/5. 477 mg of 2-bromo-6-[(1E,3E)-(5RS)-5-hydroxy-1,3-tridecadienyl]-pyridine is obtained as crude product.

Workup

  1. customdried on sodium sulfate
  2. concentrationconcentrated by evaporation
  3. customthe residue is chromatographed on silica gel with hexane/ethyl acetate=95/5

Sources & evidence

ORD record
ord-0329ac01c88e47378f4dc79ba03d0ebc
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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