Water → HCID 18507160, compound

HRID 1633546Notes

Reaction equation

HRID 1633546 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:23])([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:9][NH:10][C:11](=[O:14])[CH2:12]Cl)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[CH2:9][NH:10][C:11](=[O:14])[CH2:12][O:23]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18507128HCID 18507128, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18507160HCID 18507160, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of N-[2-(4-bromo-phenyl)-2-hydroxy-2-(3-methoxy-phenyl)-ethyl]-2-chloro-acetamide (3.67 g, 9.2 mmol), in benzene (205 mL) at room temperature was added t-BuOK (4.54 g, 40.5 mmol). The reaction mixture was stirred at room temperature for 2 h. To the mixture was added water (40 mL) and the aqueous layer was washed with CH2Cl2 (2×50 mL). The combined organic extracts were dried over MgSO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (3:1) afforded 3.34 g of 6-(4-bromo-phenyl)-6-(3-methoxy-phenyl)-morpholin-3-one. 1HNMR (400 MHz, CDCl3) δ 7.46-7.41 (comp, 2H), 7.27-7.17 (comp, 2H), 6.89-6.70 (comp, 3H), 6.69 (br, 1H), 4.10 (s, 2H), 3.93-3.80 (comp, 2H), 3.76 (s, 3H); MS (M+1) 362.1, 364.1.

Workup

  1. washthe aqueous layer was washed with CH2Cl2 (2×50 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification by flash chromatography with hexanes/EtOAc (3:1)

Sources & evidence

ORD record
ord-9583eb065a66417cb4a625ea61c42ad3
Source dataset
uspto-grants-2003_01
Patent number
US06503905B1

Reaction notes

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