Ammonium Chloride → Cyclohexyl(3,5-dimethyl-1-benzofuran-2-yl)methanol

HRID 2091126Notes

Reaction equation

HRID 2091126 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:12]=[O:13].[CH:14]1([Mg]Br)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+]>O1CCCC1>[CH:14]1([CH:12]([C:3]2[O:4][C:5]3[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=3[C:2]=2[CH3:1])[OH:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31596873,5-Dimethyl-1-benzofuran-2-carbaldehydeHCID 178419651HCID 178419651, compound

Product 1

HCID 66777213Cyclohexyl(3,5-dimethyl-1-benzofuran-2-yl)methanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (20 mL) of 3,5-dimethyl-1-benzofuran-2-carbaldehyde (1.00 g) synthesized above in tetrahydrofuran was added a 1.0M solution (8.61 mL) of cyclohexylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, tetrahydrofuran was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (25% ethyl acetate/hexane) to give the title object compound (1.13 g, 76%) as a pale-yellow solid.

Workup

  1. customto quench
  2. customthe reaction, tetrahydrofuran
  3. customwas evaporated in an evaporator
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-89f12f47284d41b69f41c4e65b4a6e07
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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