Ammonium Chloride → HCID 22382431, compound

HRID 1349451Notes

Reaction equation

HRID 1349451 reaction equation
[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.[Si:6]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Mg]Br)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[CH:1]1([CH:4]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][O:13][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:7])[CH3:8])[OH:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 123114CyclopropanecarboxaldehydeHCID 178420655HCID 178420655, compound

Product 1

HCID 22382431HCID 22382431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (2.20 g) was suspended in tetrahydrofuran (4 ml) and iodine (2 mg) was added. Thereto was added dropwise a solution of 2-bromo-1-(tert-butyldimethylsilyloxymethyl)benzene (24.0 g) obtained in Step 1 in tetrahydrofuran (10 ml) over 30 min and the reaction mixture was heated under reflux for 1 hr. Thereto was added tetrahydrofuran to give 1M 2-(tert-butyldimethylsilyloxymethyl)phenylmagnesium bromide-tetrahydrofuran solution. Then cyclopropanecarboxaldehyde (2.80 g) was dissolved in tetrahydrofuran (120 ml), and 1M 2 -(tert-butyldimethylsilyloxymethyl)phenylmagnesium bromide—tetrahydrofuran solution (80 ml) was added dropwise under ice-cooling over 50 min. The reaction mixture was stirred at room temperature for 12 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution (8 ml) under ice-cooling and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5) to give the title compound (8.20 g).

Workup

  1. temperaturecooling over 50 min
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred at room temperature for 30 min
  4. dry with materialThe reaction mixture was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-b5505794a65b40eb92c30c298e25fad1
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

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