5-[(2-Methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-carbaldehyde → Cyclohexyl{5-[(2-methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-yl}methanol

HRID 2091398Notes

Reaction equation

HRID 2091398 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:18])[C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH:14]=[O:15])=[C:11]([CH3:16])[C:10]=2[CH:17]=1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1>[CH:19]1([CH:14]([C:12]2[O:13][C:9]3[CH:8]=[CH:7][C:6]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:18])=[CH:17][C:10]=3[C:11]=2[CH3:16])[OH:15])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 866627595-[(2-Methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-carbaldehyde2×HCID 178419651HCID 178419651, compound

Product 1

HCID 66777322Cyclohexyl{5-[(2-methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-yl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (5 mL) of 5-[(2-methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-carbaldehyde (0.09 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise cyclohexylmagnesium bromide (2 mL, 1M tetrahydrofuran solution) under ice-cooling. After the completion of the dropwise addition, the ice bath was removed, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (0.11 g, quantitative) as a yellow oil.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. additionTo the reaction mixture was added aqueous ammonium chloride solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)
  8. customto give the title object compound (0.11 g, quantitative) as a yellow oil

Sources & evidence

ORD record
ord-21f5e3691eb0486d96413435aedad656
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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