Magnesium bromide diethyl etherate → HCID 22999159, compound

HRID 1166796Notes

Reaction equation

HRID 1166796 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][O:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]=[O:19])=[CH:10][CH:9]=2)[O:4][CH2:3]1.CCOCC.[Mg+2].[Br-].[Br-].[CH2:29]([Mg]Cl)[CH:30]([CH3:32])[CH3:31]>C(OCC)C.CO.O.Cl>[CH3:1][C:2]1([CH3:20])[CH2:3][O:4][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]([OH:19])[CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:10][CH:9]=2)[O:6][CH2:7]1

Participants

8

Reactant 3

HCID 9903262Magnesium bromide diethyl etherateHCID 22999173HCID 22999173, compoundHCID 178418368HCID 178418368, compound

Product 1

HCID 22999159HCID 22999159, compoundYield 36%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

4-(5,5-dimethyl-1,3-dioxan-2-yl)-1-naphthaldehyde (4.0 g, 14.8 mmol) was dissolved in diethyl ether (80 mL). Magnesium bromide diethyl etherate (2.8 g, 10.8 mol) was added followed by a 2M solution of isobutyl magnesium chloride in diethyl ether (8.0 mL, 16 mmol). The mixture was stirred at room temperature for 16 hours, diluted with methanol (1 mL), water (1 mL), and 1 N HCl (20 mL). The phases were separated, and the aqueous phase was extracted with ether (3×50 mL). The combined organic extracts were dried (MgSO4), and concentrated. Flash chromatography of the residue provided the 1.76 g (36%) desired product.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ether (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04418ac1983241fa9c34daaaefa0db92
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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