Diisobutylaluminumhydride → [4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-methanol

HRID 1677236Notes

Reaction equation

HRID 1677236 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:15]=1[CH:24]([CH3:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH3:23][O:22][C:17]1[C:18]([O:20][CH3:21])=[CH:19][C:14]([CH2:13][OH:12])=[C:15]([CH:24]([CH3:32])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 595985434,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzoic acid methyl ester

Product 1

HCID 59598568[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-methanolYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutyl aluminum hydride (22.9 mL, 1.0 M in THF) was added to a solution of 4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzoic acid methyl ester (2.886 g, 9.2 mmol) in 100 mL THF at −78° C. over 10 min. The mixture was allowed to stir for 1 h and warmed to room temperature. After 1.5 hours the mixture was quenched by the slow addition of 50 mL saturated Rochelle's salt. After rapidly stirring for 30 minutes the mixture was filtered through a pad of celite and concentrated in vacuo. H2O was added and the slurry was extracted with ethyl acetate, washed with H2O and washed with brine. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a crude oil. Purification via flash chromatography (3:1 hexane/ethyl acetate) afforded [4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-methanol as a clear oil (1.269 g, 48%).

Workup

  1. customAfter 1.5 hours the mixture was quenched by the slow addition of 50 mL saturated Rochelle's salt
  2. stirringAfter rapidly stirring for 30 minutes the mixture
  3. filtrationwas filtered through a pad of celite
  4. concentrationconcentrated in vacuo
  5. additionH2O was added
  6. extractionthe slurry was extracted with ethyl acetate
  7. washwashed with H2O
  8. washwashed with brine
  9. dry with materialThe combined organics were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give a crude oil
  13. customPurification via flash chromatography (3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c79948b661fe49e9b47232fd9cfcbefe
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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