Tetrahydrofuran toluene → HCID 178472330, compound

HRID 2368131Notes

Reaction equation

HRID 2368131 reaction equation
C1(COC2C=CC3C=[C:11]([C@H:13]4[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][C:21](N5CCOCC5)=[O:22])[CH2:15][CH2:14]4)[O:12]C=3C=2)CC1.[CH3:31][Mg]Br.[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>C1COCC1>[CH:41]1([CH2:45][O:44][C:37]2[CH:38]=[CH:39][C:34]3[CH:40]=[C:11]([C@H:13]4[CH2:14][CH2:15][C@H:16]([O:19][CH2:20][C:21](=[O:22])[CH3:31])[CH2:17][CH2:18]4)[O:12][C:35]=3[CH:36]=2)[CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, compoundHCID 178521450HCID 178521450, compound

Product 1

HCID 178472330HCID 178472330, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[({trans-4-[6-(cyclopropylmethoxy)-1-benzofuran-2-yl]cyclohexyl}oxy)acetyl]morpholine (881 mg) in THF (10 mL) was added a solution (1.5 M, 2.84 mL) of methylmagnesium bromide in toluene/THF under ice-cooling. The mixture was stirred at 0° C. for 1 hr and extracted with ethyl acetate and 1M hydrochloric acid. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (556 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate and 1M hydrochloric acid
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f315c2fe6a004c1a9ecb134f34e83d81
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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