Water → Ethyl (2E)-3-(4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoate

HRID 1992854Notes

Reaction equation

HRID 1992854 reaction equation
[Li]CCCC.[CH2:6]([C:8]1[C:9]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:10]([O:20][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=2)[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2)[CH3:7].[OH2:35].[CH2:36]1[CH2:40][O:39][CH2:38][CH2:37]1>>[CH2:6]([C:8]1[C:9]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:10]([O:20][C:21]2[CH:28]=[CH:27][C:24](/[CH:25]=[CH:37]/[C:38]([O:39][CH2:40][CH3:36])=[O:35])=[CH:23][CH:22]=2)[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2)[CH3:7]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 860871094-{[3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 86616647Ethyl (2E)-3-(4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoateYield 94%

Conditions

Temperature
-78 °C

Procedure

Triethylphosphonoacetate (0.44 g, 1.89 mmol) was dissolved in THF (12 mL). Cooled to −78° C., nBuLi (1.6 M in hexanes, 1.20 mL, 1.89 mmoL) was added dropwise. The mixture was stirred at −78° C. for 30 min. To this solution was added 4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehyde (58) (0.60 g, 1.58 mmol) in THF (12 mL) slowly. The resulting mixture was allowed to warm up to room temperature and stirred at room temperature (3 h in total). The mixture was poured into water (50 mL) and extracted with EtOAc (2×50 mL). The extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (25:1) to give 0.67 g (94%) of the title compound (59) as a white foam. 1H NMR (400 MHz, CDCl3): δ 1.12 (t, J=7.5 Hz, 3H), 1.30 (t, J=7.2 Hz, 3H), 2.56 (q, J=7.5 Hz, 2H), 3.93 (s, 3H), 4.22 (q, J=7.2 Hz, 2H), 6.21 (d, J=16.0 Hz, 1H), 6.56 (d, J=8.6 Hz, 2H), 7.04 (dd, J1=8.6 Hz, J2=2.4 Hz, 1H), 7.10-7.20 (m, 3H), 7.20-7.27 (m, 5H), 7.54 (d, J=16.0 Hz, 1H), 7.59 (s, 1H), 7.72 (d, J=9.2 Hz, 1H). LCMS (APCI): m/z 453 (M+H)+.

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirred at room temperature (3 h in total)
  3. extractionextracted with EtOAc (2×50 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customto give the crude product as a light yellow oil
  9. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (25:1)

Sources & evidence

ORD record
ord-c0eae89bcb0e435fbfecb15fcdd13033
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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