Ammonium Chloride → HCID 15054015, compound

HRID 1198526Notes

Reaction equation

HRID 1198526 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[N+:20]([O-])=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]2[C:14]=1[NH:20][CH:2]=[CH:1]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 361282HCID 361282, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 15054015HCID 15054015, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

M Vinyl magnesium bromide solution in tetrahydrofuran (80 ml) was added to a stirred solution of 2-benzyloxy-5-chloronitrobenzene (5.28 g, 20 mmol) in tetrahydrofuran (160 ml) at -40° C. The mixture was stirred for 2 hours at -40° C. then poured onto saturated ammonium chloride solution (500 ml) and extracted with ether. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:8) to give a yellow oil.

Workup

  1. extractionextracted with ether
  2. customThe extract was dried
  3. customevaporated
  4. customthe residue was chromatographed on silica in ethyl acetate-hexane (1:8)
  5. customto give a yellow oil

Sources & evidence

ORD record
ord-797e5ce64fbe45e8a94af18b4413e57c
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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