Ammonium Chloride → HCID 21189060, compound

HRID 1383867Notes

Reaction equation

HRID 1383867 reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[C:12]([CH3:14])=[O:13].[Cl-].[NH4+]>O1CCCC1>[CH3:14][C:12]([C:6]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=1[CH3:4])([OH:13])[CH3:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 701334-Hydroxy-2-methylacetophenoneHCID 178418573HCID 178418573, compound

Product 1

HCID 21189060HCID 21189060, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a solution of methylmagnesium bromide (30 ml, 90 mmol, 3M solution) dissolved in tetrahydrofuran (15 ml), a solution of compound (16) (4.5 g, 30 mmol) dissolved in tetrahydrofuran (10 ml) was slowly added dropwise at −78° C. When the dropping was completed, was slowly heated to −40° C., and stirred for 5 hours. After heating to 0° C., the solution was stirred for one hour, and then, ammonium chloride (50 ml) was slowly added dropwise thereto. The reaction solution was extracted with organic solvent, washed, dried and purified by using column chromatography (eluent: hexane/ethyl acetate=10/1) to obtain 4.0 g (80%) of pure compound (17).

Workup

  1. additionwas slowly added dropwise at −78° C
  2. temperatureAfter heating to 0° C.
  3. stirringthe solution was stirred for one hour
  4. extractionThe reaction solution was extracted with organic solvent
  5. washwashed
  6. customdried
  7. custompurified

Sources & evidence

ORD record
ord-547940a900e6472da2900376f8a89f26
Source dataset
uspto-grants-2001_07
Patent number
US06255517B1

Reaction notes

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