Ammonium Chloride → HCID 11818538, compound

HRID 1951758Notes

Reaction equation

HRID 1951758 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH2:6]([N:13]=[C:14]1[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[NH4+]>ClCCl>[CH2:3]([C:14]1([NH:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:23][CH2:22][C:17]2([O:18][CH2:19][CH2:20][O:21]2)[CH2:16][CH2:15]1)[CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11043015HCID 11043015, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 11818538HCID 11818538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 M solution of allylmagnesium bromide (127 ml, 127 mmol) was added dropwise to a solution of benzyl-(1,4-dioxaspiro[4.5]dec-8-ylidene)amine (15.6 g, 63.7 mmol) in dichloromethane (120 ml), and the reaction mixture was stirred for 72 h at room temperature. The mixture was then poured carefully onto saturated ammonium chloride solution (100 ml), while cooling with ice, and extraction with dichloromethane (3×40 ml) was carried out. The combined organic phases were dried with sodium sulfate and concentrated in vacuo, and the residue was purified by flash chromatography (400 g, 20×7.6 cm) with chloroform/methanol (10:0.2).

Workup

  1. dry with materialThe combined organic phases were dried with sodium sulfate
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by flash chromatography (400 g, 20×7.6 cm) with chloroform/methanol (10:0.2)

Sources & evidence

ORD record
ord-8b23c8327af94b528144ad19bfb946cf
Source dataset
uspto-grants-2013_03
Patent number
US08404740B2

Reaction notes

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