Ammonium Chloride → HCID 14416771, compound

HRID 1816945Notes

Reaction equation

HRID 1816945 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[O:6][CH2:5][CH2:4][O:3]1.[CH3:12][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[CH3:10][C:9]([OH:11])([CH2:8][CH2:7][C:2]1([CH3:1])[O:3][CH2:4][CH2:5][O:6]1)[CH3:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5383774-(2-Methyl-1,3-dioxolan-2-yl)-2-butanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 14416771HCID 14416771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The obtained 4-(2-methyl[1,3]dioxolan-2-yl)butan-2-one (27.60 g) was dissolved in tetrahydrofuran (220 ml), and thereafter, methylmagnesium bromide (3 M tetrahydrofuran solution; 85 ml) was added to the solution at a room temperature. The obtained mixture was stirred for 40 minutes, and an aqueous saturated ammonium chloride solution (300 ml) was then added thereto, followed by extraction with ethyl acetate (300 ml×3). The organic layer was washed with a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was then distilled off under a reduced pressure. The residue was purified by silica gel column chromatography (eluted with ethyl acetate-hexane (1:1)) to obtain 2-methyl-4-(2-methyl[1,3]dioxolan-2-yl)butan-2-ol (21.18 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (300 ml×3)
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluted with ethyl acetate-hexane (1:1))

Sources & evidence

ORD record
ord-d771492979954edd8cb65726e067af1c
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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