Isopropanol → HCID 69203197, compound

HRID 2378310Notes

Reaction equation

HRID 2378310 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH:24]=[O:25])[CH3:19].C(O)(C)C>C1COCC1.O>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([CH:24]([C:23]2[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:21]([O:20][CH2:18][CH3:19])[CH:22]=2)[OH:25])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH3:12]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 217726904-Bromo-2-ethoxy-1-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 69203197HCID 69203197, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A stirred mixture of 4-bromo-2-ethoxy-1-methoxy-benzene (6.52 g, 28.2 mmol) and dry THF (40 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (11.3 mL, 28.2 mmol) and stirred for 30 min. Then a mixture of 3-ethoxy-4-methoxy-benzaldehyde (4.62 g, 25.7 mmol) in dry THF (60 mL) was added and stirred for 1 h at −78° C. The mixture was quenched with isopropanol (11.7 mL, 154 mmol) and added water (30 mL). It was extracted with ether (3×50 mL). The combined organic phases were washed with water (2×50 mL), dried over MgSO4 and concentrated to an oil, which was purified by flash column chromatography (EtOAc/Hexane) to give bis-(3-ethoxy-4-methoxy-phenyl)-methanol as an oil (8.85 g, 100% yield): 1H NMR (CDCl3) δ 1.44 (t, J=7 Hz, 6H, 2CH2CH3), 2.12 (d, J=4 Hz, 1H, OH), 3-0.86 (s 6H, 2OCH3), 4.06 (q, J=7 Hz, 4H, 2CH2CH3), 5.74 (d, J=4 Hz, 1H, CH), 6.81-6.91 (m, 6H, Ar). The product was used in the next step without further purification.

Workup

  1. customevacuated
  2. additionrefilled with nitrogen for 10 cycles
  3. additionwas added
  4. stirringstirred for 1 h at −78° C
  5. extractionIt was extracted with ether (3×50 mL)
  6. washThe combined organic phases were washed with water (2×50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to an oil, which
  9. customwas purified by flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-2950945823d94551aca7466880a8867e
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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