Water → 1-[4-(Diethoxymethyl)phenyl]-1-[4-(methoxymethoxy)phenyl]-2-phenylbutan-1-ol

HRID 2118212Notes

Reaction equation

HRID 2118212 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)[CH3:2].[Li]CCCC.[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:40])[CH:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][CH3:33])=[CH:26][CH:25]=1.O>C1COCC1>[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][C:8]([C:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][O:21][CH3:20])=[CH:29][CH:28]=2)([OH:40])[CH:31]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:32][CH3:33])=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6883401-Bromo-4-(diethoxymethyl)benzeneHCID 588776611-[4-(Methoxymethoxy)phenyl]-2-phenylbutan-1-oneHCID 178418339Butyllithium

Product 1

HCID 693166761-[4-(Diethoxymethyl)phenyl]-1-[4-(methoxymethoxy)phenyl]-2-phenylbutan-1-olYield 122.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-bromobenzaldehyde diethyl acetal (107 g, 0.41 mol) in anhydrous THF (750 mL) was added n-BuLi (1.6 M in hexanes, 268 mL, 0.43 mol) dropwise at −78° C. After stirring for 1 h at −78° C., a solution of 15 (97.6 g, 0.34 mol) in THF (750 mL) was cannulated into the reaction mixture portionwise. The mixture was stirred overnight at RT, H2O (500 mL) was added, and the volatiles were removed under reduced pressure. The residue was extracted with Et2O (3×500 mL) and the combined extracts washed with H2O (500 mL) and brine (500 mL). The mixture was dried over MgSO4 and concentrated to afford 194 g of 16 that was used without further purification. 1HNMR (400 MHz, DMSO-d6): δ 0.58 (t, J=7.3 Hz, 3H), 1.12 (m, 6H), 1.52 (m, 1H), 1.70 (m, 1H), 3.23 (s, 3H), 3.40-3.65 (m, 5H), 4.98 (s, 2H), 5.41 (s, 1H), 5.51 (s, 1H), 6.62 (d, J=8.8 Hz, 2H), 6.96-7.06 (m, 3H), 7.17-7.23 (m, 4H), 7.31 (d, J=8.0 Hz, 2H), 7.61 (d, J=8.4 Hz, 2H).

Workup

  1. stirringThe mixture was stirred overnight at RT
  2. customthe volatiles were removed under reduced pressure
  3. extractionThe residue was extracted with Et2O (3×500 mL)
  4. washthe combined extracts washed with H2O (500 mL) and brine (500 mL)
  5. dry with materialThe mixture was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4b5d93fe3a684d8581ea760248b6df69
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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