Water → HCID 86616658, compound

HRID 1992913Notes

Reaction equation

HRID 1992913 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:19][CH2:20][CH3:21])[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]2[OH:12])=[CH:4][C:3]=1[O:22][CH3:23].F[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:19][CH2:20][CH3:21])[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]2[O:12][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=2)=[CH:4][C:3]=1[O:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 68538747HCID 68538747, compound

Product 1

HCID 86616658HCID 86616658, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

7-Fluoro-6-(methyloxy)-2-phenyl-3-propyl-1-naphthalenol (137) (0.42 g, 1.34 mmol) was dissolved in DMF (5 mL). To this solution was added 4-fluorobenzaldehyde (0.34 g, 2.68 mmol) followed by Cs2CO3 (0.57 g, 1.74 mmol). The mixture was heated at 100° C. for 36 h, poured into water (50 mL) and extracted with EtOAc (2×75 mL). The combined organic extract was washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as reddish brown oil. The crude product was purified by flash chromatography over SiO2 eluted with a gradient from hexanes to 15% EtOAc in hexanes to give 0.38 g (69%) of the title compound (138) as a yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.81 (t, J=7.4 Hz, 3H), 1.40-1.60 (m, 2H), 2.53 (t, J=7.8 Hz, 2H), 4.02 (s, 3H), 6.66 (d, J=8.8 Hz, 2H), 7.06-7.12 (m, 2H), 7.18-7.25 (m, 4H), 7.40 (d, J=12.1 Hz, 1H), 7.56-7.64 (m, 3H), 9.80 (s, 1H). LCMS (ESI): m/z 415 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×75 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as reddish brown oil
  8. customThe crude product was purified by flash chromatography over SiO2
  9. washeluted with a gradient from hexanes to 15% EtOAc in hexanes

Sources & evidence

ORD record
ord-c909a8c6bb414e2f8402b5862566fa34
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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