4'-Methoxyacetophenone → HCID 24815140, compound

HRID 603362Notes

Reaction equation

HRID 603362 reaction equation
[Li+].CC([N-]C(C)C)C.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1.[C:20]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].[NH4+].[Cl-]>O1CCCC1>[C:20]([C:24]1[CH:25]=[CH:26][C:27]([CH:28]([OH:29])[CH2:18][C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[O:19])=[CH:30][CH:31]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 74764'-MethoxyacetophenoneHCID 25517Ammonium ChlorideHCID 703244-tert-ButylbenzaldehydeHCID 2724682Lithium diisopropylamide

Product 1

HCID 24815140HCID 24815140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

4.0 ml of LDA 1M in THF (4.0 mmol) are added under nitrogen to a solution of p-methoxyacetophenone (500 mg, 3.3 mmol) in THF (tetrahydrofuran) (15 ml) at −78° C. The mixture is stirred for 1 h before 5 ml of a THF solution of p-tert-butylbenzaldehyde (594 mg, 3.7 mmol) are added. The reaction is allowed to reach −40° C. over the course of 1 h. A cold aqueous solution of NH4Cl 1N is subsequently added to the reaction mixture. The resultant mixture is partitioned between water (30 ml) and dichloromethane (30 ml). The resultant aqueous phase is subsequently extracted with dichloromethane (2×30 ml). The combined organic phases are dried over MgSO4. Removal of the solvent gives 3-(4-tert-butylphenyl)-3-hydroxy-1-(4-methoxyphenyl)propan-1-one.

Workup

  1. additionare added
  2. customto reach −40° C. over the course of 1 h
  3. customThe resultant mixture is partitioned between water (30 ml) and dichloromethane (30 ml)
  4. extractionThe resultant aqueous phase is subsequently extracted with dichloromethane (2×30 ml)
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-504002e70a394bd7b6fe982fee9a5913
Source dataset
uspto-grants-2011_03
Patent number
US07906684B2

Reaction notes

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