Pentane → HCID 66759808, compound

HRID 1850401Notes

Reaction equation

HRID 1850401 reaction equation
CCCCC.[C:6]([Li])([CH3:9])([CH3:8])[CH3:7].C1COCC1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[C:31]([CH3:44])=[C:32]([CH3:43])[C:33]4[O:37][C:36]([CH3:39])([CH3:38])[C:35](=[O:40])[C:34]=4[C:41]=3[CH3:42])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>O>[C:6]([C:35]1([OH:40])[C:34]2[C:41]([CH3:42])=[C:30]([N:27]3[CH2:26][CH2:25][N:24]([C:21]4[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:23][CH:22]=4)[CH2:29][CH2:28]3)[C:31]([CH3:44])=[C:32]([CH3:43])[C:33]=2[O:37][C:36]1([CH3:39])[CH3:38])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 8003PentaneHCID 8028TetrahydrofuranHCID 229355955-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-oneHCID 178418306HCID 178418306, compound

Product 1

HCID 66759808HCID 66759808, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A pentane solution (2.00 mL, 3.08 mmol) containing 1.54 M t-butyllithium was added dropwise to a solution of THF (4 mL) containing 5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one (800 mg, 2.03 mmol) synthesized in Reference Example 42 under argon atmosphere at −70° C. or lower, and then the mixture was warmed to 0° C. The reaction solution was stirred under ice-cooling condition for 30 minutes, and then water was added thereto and extraction was performed using ethyl acetate. The organic layer was washed with water and saturated saline, and then dried using anhydrous sodium sulfate. It was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane-ethyl acetate 100:0 to 8:1) and silica gel column chromatography (hexane-ethyl acetate 100:0 to 8:1), and after that, crystallization was performed using hexane to give 300 mg of the title compound (yield: 33%).

Workup

  1. customsynthesized in Reference Example 42 under argon atmosphere at −70° C.
  2. temperaturecooling condition for 30 minutes
  3. extractionextraction
  4. washThe organic layer was washed with water and saturated saline
  5. customdried
  6. concentrationIt was concentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (hexane-ethyl acetate 100:0 to 8:1) and silica gel column chromatography (hexane-ethyl acetate 100:0 to 8:1)
  8. customafter that, crystallization

Sources & evidence

ORD record
ord-8b0ec38517784f8b9fa5054ae4f6a8b4
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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