Ammonium Chloride → HCID 67146635, compound

HRID 2422247Notes

Reaction equation

HRID 2422247 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1.[CH3:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:16]=1[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1.II>[CH3:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:16]=1[CH:17]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1)[OH:18]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5838412,6-DimethylbenzaldehydeHCID 27738422-(4-Bromophenyl)-1,3-dioxolaneHCID 5462224Magnesium

Product 1

HCID 67146635HCID 67146635, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Iodine (10 mg) was added to a mixture of magnesium (1.20 g) and tetrahydrofuran (50 mL) with vigorous stirring and 2-(4-bromophenyl)-1,3-dioxolane (10.0 g) was added dropwise at room temperature. After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 1 hr and a solution of 2,6-dimethylbenzaldehyde (5.0 g) in tetrahydrofuran (20 mL) was added dropwise at 0° C. After the completion of the dropwise addition, the temperature of the reaction mixture was allowed to return to room temperature and the mixture was further stirred for 1 hr. The reaction mixture was poured into saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated and the residue was purified by silica gel column chromatography. The residue was developed with ethyl acetate-hexane (gradient of 1:9 to 7:3 by volume ratio) to give the title compound (9.10 g, yield 73%) as a yellow oil.

Workup

  1. additionAfter the completion of the dropwise addition
  2. stirringthe reaction mixture was stirred at room temperature for 1 hr
  3. additionAfter the completion of the dropwise addition
  4. customto return to room temperature
  5. stirringthe mixture was further stirred for 1 hr
  6. extractionthe mixture was extracted with ethyl acetate
  7. concentrationThe ethyl acetate layer was concentrated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bfb3f2f87ba242ea826c76bde56268ea
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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