Benzyl Alcohol → HCID 58026930, compound

HRID 1966288Notes

Reaction equation

HRID 1966288 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:12][C:13]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([CH3:33])=[CH:16][C:17]([CH3:32])([CH3:31])[NH:18]2.C(OCC)(=O)C>O1CCCC1>[CH2:3]([O:10][CH2:12][C:13]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([CH3:33])=[CH:16][C:17]([CH3:32])([CH3:31])[NH:18]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 58027060HCID 58027060, compound2×

Product 1

HCID 58026930HCID 58026930, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

60% Sodium hydride (30 mg, 0.75 mmol) was suspended in anhydrous tetrahydrofuran (1 mL), and benzylalcohol (78 μL, 0.75 mmol) was added thereto under argon atmosphere at 0° C. After the reaction mixture was stirred at room temperature for 30 minutes, a solution of 5-chloromethyl-6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound 5-1, 50 mg, 0.15 mmol) in anhydrous tetrahydrofuran solution (1.5 mL) was added thereto. The reaction mixture was stirred at 50° C. for 7 hours. After cooling down, ethyl acetate (50 mL) was added thereto. The whole was washed with water (50 mL) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (4.0 mg) as a colorless solid. (Yield 7%)

Workup

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at 50° C. for 7 hours
  3. temperatureAfter cooling down
  4. washThe whole was washed with water (50 mL) and saturated brine (30 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-93f14ee2886e46d0aaaf4c0c1a89a0bd
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

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