Sodium Hydroxide → HCID 68744497, compound

HRID 1958749Notes

Reaction equation

HRID 1958749 reaction equation
[OH-].[Na+].[C:3]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18]CCCCCC)[CH:13]=1)(=O)[C:4]1C=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([O:33][CH3:34])[O:31][CH3:32]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].O>[CH3:32][O:31][CH:30]([O:33][CH3:34])[CH2:29][CH2:28][CH2:27][CH2:26][O:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 110746845-bromo-1,1-dimethoxypentaneHCID 68742730HCID 68742730, compound

Product 1

HCID 68744497HCID 68744497, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of NaOH (100 mg, 2.5 mmol), n-Bu4NI (37 mg, 0.1 mmol), 3-(hexyloxy)phenyl benzoate (ref. Prasad K. et al. Org. Proc. Res. Dev., 2003, 7 (5), 743-749) (200 mg, 0.67 mmol) in H2O (3 mL) was evacuated and refilled with Ar three times. The reaction mix was heated with stirring to 90° C. under Ar and treated with 5-bromo-1,1-dimethoxypentane (0.24 g, 1.2 mmol), added dropwise over 30 min at 95° C. Stirring was continued at 95° C. overnight. Later, the reaction mixture was cooled to rt and extracted with Et2O (2×). The organic extracts were washed (2 M aq NaOH, brine), concentrated under reduced pressure and purified by flash chromatography on silica gel using 0-7% EtOAc/hexanes as the eluent to afford the title compound as a colorless oil (127 mg, 59%). 1H NMR (400 MHz, CDCl3) δ ppm 7.15 (t, J=8.08 Hz, 1 H), 6.43-6.52 (m, 3 H), 4.89 (t, J=4.67 Hz, 1 H), 3.82-4.03 (m, 10 H), 1.20-1.92 (m, 14 H), 0.91 (t, J=6.82 Hz, 3 H).

Workup

  1. customwas evacuated
  2. additionrefilled with Ar three times
  3. additionThe reaction mix
  4. temperaturewas heated
  5. additionadded dropwise over 30 min at 95° C
  6. stirringStirring
  7. temperatureLater, the reaction mixture was cooled to rt
  8. extractionextracted with Et2O (2×)
  9. washThe organic extracts were washed (2 M aq NaOH, brine)
  10. concentrationconcentrated under reduced pressure
  11. custompurified by flash chromatography on silica gel using 0-7% EtOAc/hexanes as the eluent

Sources & evidence

ORD record
ord-5d3f3c717192460db26b29139e18a4e0
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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