Water → HCID 58847340, compound

HRID 1272334Notes

Reaction equation

HRID 1272334 reaction equation
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:19]([CH3:39])=[C:20]([CH:37]=[O:38])[C:21]4[O:25][C:24]([CH3:27])([CH3:26])[CH:23]([C:28]5[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=5)[C:22]=4[C:35]=3[CH3:36])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.O>C1COCC1>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:19]([CH3:39])=[C:20]([CH:37]([OH:38])[CH3:1])[C:21]4[O:25][C:24]([CH3:27])([CH3:26])[CH:23]([C:28]5[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=5)[C:22]=4[C:35]=3[CH3:36])[CH2:14][CH2:13]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 58847342HCID 58847342, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58847340HCID 58847340, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl magnesium bromide (THF solution 3.0 M, 1.0 mL, 3.0 mmol) in THF (5 ml) at −30° C. was added 5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6-tetramethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-7-carbaldehyde (310 mg, 640 mmol) obtained in Example 105. The reaction mixture was stirred for 20 minutes under the same temperature. The resulting mixture was poured into water and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane-ethyl acetate to obtain 19.5 mg (yield 61%) of the title compound. mp. 149–151° 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. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-706bc21ddd1e4acbbdaa09e99ba8746b
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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