Water → HCID 10116596, compound

HRID 1633450Notes

Reaction equation

HRID 1633450 reaction equation
[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[O:25][CH2:24][CH:23]=[CH:22][C:17]4=3)[NH:12][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:28]([CH2:35][CH2:36][CH2:37][CH2:38]Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[O:25][CH2:24][CH:23]=[CH:22][C:17]4=3)[N:12]([CH2:38][CH2:37][CH2:36][CH2:35][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 70986(4-Bromobutoxy)benzeneHCID 9862338HCID 9862338, compound

Product 1

HCID 10116596HCID 10116596, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing the compound of Example 3 (0.08 g., 0.24 mmol) in N,N-dimethylformamide (5.00 mL) was added sodium hydride (0.011 g., 60% in oil, 0.29 mmol) at 0° C. The mixture was stirred at room temperature for 20 minutes, then cooled to 0° C. 4-Phenoxybutyl bromide (0.072 g., 0.32 mmol) was added to the mixture, the resulting mixture was stirred at room temperature for 16 hours. Water and ethyl acetate then were added to the mixture, and the organic and aqueous phases were separated. The aqueous layer then was extracted with ethyl acetate (2×). The combined ethyl acetate solution was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo. The residue was subjected to preparative thin layer chromatography (silica gel, 50% EtOAc/hexane) to yield the alkylated compound (0.033 g, 29%) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.42, 7.13, 7.03, 6.95, 6.87, 6.71, 5.81, 4.69-4.67, 4.09, 3.93, 3.75, 3.17-3.14, 2.97-2.94, 1.87-1.76; MS (ESI+) m/z 479 (M++1).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe resulting mixture was stirred at room temperature for 16 hours
  3. customthe organic and aqueous phases were separated
  4. extractionThe aqueous layer then was extracted with ethyl acetate (2×)
  5. dry with materialThe combined ethyl acetate solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-60c96e541ffd49828713121b8ae6bfeb
Source dataset
uspto-grants-2003_01
Patent number
US06503899B2

Reaction notes

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