Ammonium Chloride → HCID 14349141, compound

HRID 414848Notes

Reaction equation

HRID 414848 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:34])([CH3:33])[C:13]([C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[O:18][CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][Mg]Br.[Cl-].[NH4+]>CCOCC>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:34])([CH3:33])[C:13]([C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[O:18][CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1)([CH3:35])[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 54496858HCID 54496858, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 14349141HCID 14349141, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the ketone, 2-(3-(6-phenoxy-2,2-dimethyl hexanoyl)phenoxymethyl) quinoline (3.6 g) in dry ether (100 ml) at 0° C., was added dropwise, an ethereal solution of methyl magnesiumbromide (7.7 ml, 23.8 mmol, 3 eqv.) under an atmosphere of nitrogen. The clear orange solution was stirred overnight at room temperature. To this solution, a saturated ammonium chloride solution was added when the magnesium salts precipitated. The ether layer was separated, washed with water and brine, and then dried over MgSO4. All volatiles were removed to obtain the crude product (4.2 g). This was purified by chromatography on silica gel (25% ethyl acetate in hexanes, 20% ethyl acetate in hexanes and finally 10% ethyl acetate in hexanes) to obtain the pure product as a yellow liquid (0.9 g).

Workup

  1. customprecipitated
  2. customThe ether layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customAll volatiles were removed
  6. customto obtain the crude product (4.2 g)
  7. customThis was purified by chromatography on silica gel (25% ethyl acetate in hexanes, 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c8ff099e82bc491f840485b859e8fe0c
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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