Water → HCID 60167282, compound

HRID 2281863Notes

Reaction equation

HRID 2281863 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:17])=[CH:5][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[CH2:24]([O:17][C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[Br:1])[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10541874HCID 10541874, compound

Product 1

HCID 60167282HCID 60167282, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Naphthol 7 (3.20 g, 11.0 mmol) was dissolved in anhydrous DMF (78 mL). K2CO3 (3.05 g, 22.0 mmol), benzyl bromide (1.59 mL, 13.2 mmol), and Bu4NI (163 mg, 0.440 mmol) were added. The solution was stirred at 25° C. for 16 h. The reaction mixture was poured into H2O and extracted with ethyl acetate (3×). The organic extracts were combined, dried over Na2SO4, and concentrated under reduced pressure. The solid was recrystallized with 5% EtOAc/hexanes and the mother liquor was further purified by flash chromatography (SiO2, 6×15 cm, 10-20% EtOAc/hexanes gradient elution) affording additional 8 (3.30 g combined, 77%) as a brown crystalline solid. 1H NMR (CDCl3 500 MHz) δ 8.17 (s, 1H), 7.87 (d, J=7.5 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.61 (d, J=7.5 Hz, 2H), 7.57 (s, 1H), 7.40 (t, J=7.5 Hz, 2H), 7.35-7.32 (m, 1H), 7.29 (t, J=7.5 Hz, 1H), 5.30 (s, 2H), 4.43 (q, J=7.0 Hz, 2H), 1.44 (t, J=7.0 Hz, 3H). 13C NMR (CDCl3, 125 MHz) δ 166.0, 154.5, 136.1, 136.0, 135.0, 129.3, 128.3, 128.0 (2C), 127.8, 126.8, 125.8, 124.1, 116.7, 106.9, 71.2, 61.1. IR (film) νmax 2980, 1712, 1413, 1236 cm−1. ESI-TOF HRMS m/z 385.0433 (M+H+, C20H17BrO3 requires 385.0434).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe solid was recrystallized with 5% EtOAc/hexanes
  5. customthe mother liquor was further purified by flash chromatography (SiO2, 6×15 cm, 10-20% EtOAc/hexanes gradient elution)
  6. customaffording additional 8 (3.30 g combined, 77%) as a brown crystalline solid

Sources & evidence

ORD record
ord-6f945567096d460a8a778e467eca0494
Source dataset
uspto-grants-2015_09
Patent number
US09139596B2

Reaction notes

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