Diethyl Ether → 1-(2,2,3,4,6,7-Hexamethyl-3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine

HRID 1272282Notes

Reaction equation

HRID 1272282 reaction equation
C[Li].[CH2:3](OCC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:23]([CH3:36])=[C:24]([CH3:35])[C:25]4[O:29][C:28]([CH3:31])([CH3:30])[C:27](=[O:32])[C:26]=4[C:33]=3[CH3:34])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1>C1COCC1.O>[CH3:30][C:28]1([CH3:31])[C:27]([CH3:3])([OH:32])[C:26]2[C:33]([CH3:34])=[C:22]([N:19]3[CH2:18][CH2:17][N:16]([C:13]4[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:15][CH:14]=4)[CH2:21][CH2:20]3)[C:23]([CH3:36])=[C:24]([CH3:35])[C:25]=2[O:29]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 229355955-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 229356081-(2,2,3,4,6,7-Hexamethyl-3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazineYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyllithium in diethyl ether (1.14 M, 5.60 mL, 6.38 mmol) was added dropwise to a solution of 4-(4-methoxyphenyl)-1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-on-5-yl)piperazine (2.00 g, 5.06 mmol) obtained in Reference Example 13 in THF (20 ml) under ice cooling and the mixture was stirred for 10 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from hexane to obtain 2.00 g (yield 96%) of the title compound. mp. 139–141° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-ef7193bc13b943a5a2c4daaa32965aa8
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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