Water → HCID 67322163, compound

HRID 705433Notes

Reaction equation

HRID 705433 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.O>C(Cl)Cl>[CH3:14][O:13][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([CH2:2][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoate

Product 1

HCID 67322163HCID 67322163, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(bromomethyl)-4-methoxybenzoate (960 mg, 3.7 mmol) in DCM (18.5 mL) was added morpholine (0.68 mL, 7.8 mmol). The reaction mixture was stirred at room temperature overnight and poured onto iced water. The aqueous mixture was extracted with DCM (3×), and the combined organics were dried over MgSO4, filtered, and concentrated in vacuo to provide a yellow oil. The crude material was purified by flash chromatography on silica using a gradient of EtOAc in hexane (0 to 50%) as eluant. The tittle product was obtained as a clear oil (490 mg, 50%)

Workup

  1. extractionThe aqueous mixture was extracted with DCM (3×)
  2. dry with materialthe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a yellow oil
  6. customThe crude material was purified by flash chromatography on silica using a gradient of EtOAc in hexane (0 to 50%) as eluant

Sources & evidence

ORD record
ord-3d0c0192dba54797b9b66cb41ca3d6ca
Source dataset
uspto-grants-2015_11
Patent number
US09174949B2

Reaction notes

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