Ammonium Chloride → 1-[4-(Diethoxymethyl)phenyl]-1-(4-methoxyphenyl)-2-phenylbutan-1-ol

HRID 2118202Notes

Reaction equation

HRID 2118202 reaction equation
[Mg].[CH2:2]([O:4][CH:5]([O:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)[CH3:3].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:34])[CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH3:27])=[CH:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1.O>[CH2:2]([O:4][CH:5]([O:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)([OH:34])[CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH3:27])=[CH:8][CH:7]=1)[CH3:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6883401-Bromo-4-(diethoxymethyl)benzeneHCID 36421811-(4-Methoxyphenyl)-2-phenylbutan-1-oneHCID 5462224Magnesium

Product 1

HCID 588776601-[4-(Diethoxymethyl)phenyl]-1-(4-methoxyphenyl)-2-phenylbutan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium turnings (9.64 g, 397 mmol) were heated to 160° C. under vacuum for 2 hours, then were cooled to RT under nitrogen. THF (400 mL) was added followed by portionwise addition of 4-bromobenzaldehyde diethyl acetal (80.0 mL, 393 mmol). The mixture was heated with a heat gun to initiate the reaction, then allowed to stir at RT (while gently refluxing) for 90 min. The resulting dark red solution was cooled to 0° C. and a solution of 2 (77.27 g, 304 mmol) in THF (50 mL) was added. The mixture was stirred at RT for 3 hours. Saturated aqueous NH4Cl (150 mL) and H2O (150 mL) were added and the two layers were separated. The aqueous layer was extracted with Et2O (3×100 mL), and the combined organics were dried (MgSO4) and concentrated to provide 3 as a light yellow oil that was carried on without further purification. 1H NMR (400 MHz, CDCl3): δ 0.72 (t, J=7.3 Hz, 3H), 1.25 (t, J=7.0 Hz, 6H), 1.77 (q, J=7.3 Hz, 2H), 2.35 (s, 1H), 3.69 (s, 3H), 3.52-3.65 (m, 5H), 5.50 (s, 1H), 6.62 (d, J=8.8 Hz, 2H), 7.08 (m, 1H), 7.12 (m, 6H), 7.44 (d, J=8.2 Hz, 2H), 7.53 (d, J=8.2 Hz, 2H).

Workup

  1. temperatureThe mixture was heated with a heat gun
  2. customthe reaction
  3. temperaturewhile gently refluxing) for 90 min
  4. temperatureThe resulting dark red solution was cooled to 0° C.
  5. stirringThe mixture was stirred at RT for 3 hours
  6. customthe two layers were separated
  7. extractionThe aqueous layer was extracted with Et2O (3×100 mL)
  8. dry with materialthe combined organics were dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-88ab2728e15b47ac85b58f17d46837d3
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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