Water → HCID 66842512, compound

HRID 252327Notes

Reaction equation

HRID 252327 reaction equation
C(OP([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([CH2:18][CH2:19][CH3:20])=[C:12]([O:21][CH3:22])[CH:11]=1)(=O)OCC)C.[H-].[Na+].[F:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O.O>C1COCC1>[CH3:17][O:16][C:14]1[CH:15]=[C:10]([CH:9]=[CH:28][C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[F:25])[CH:11]=[C:12]([O:21][CH3:22])[C:13]=1[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67970o-FluorobenzaldehydeHCID 86036824HCID 86036824, compound

Product 1

HCID 66842512HCID 66842512, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl(3,5-dimethoxy-4-1-propylbenzyl)phosphonate (0.50 g, 1.5 mmol) in THF (10 mL) at 0° C. was added NaH (60% in mineral oil) (0.14 g, 3.5 mmol) under N2. After the addition was completed, the suspension was stirred at 0° C. for 1 h and then 2-fluorobenzaldehyde (0.2 mL, 1.9 mmol) in THF (10 mL) was added. The reaction was kept at 0° C. for 1 h and then at 50° C. for 5 h. The reaction was cooled to 0° C. Water (5 mL) was added slowly to quench the reaction followed by addition of 2N HCl (8 mL). The mixture was extracted with ether (3×20 mL). The extract was dried over anhydrous Na2SO4. Evaporation of ether followed by flash chromatography using 5% ethyl acetate in hexane as eluent afforded 2-(3,5-dimethoxy-4-1-propylphenyl)-1-(2-fluorophenyl)ethene (1). (0.31 g, 68%) as a yellow crystal. 1HNMR (CDCl3, ppm): δ 1.34 (d, J=7.1 Hz, 6H), 3.60 (qint. J=7.1 Hz, 1H), 3.89 (s, 6H), 6.74 (s, 2H), 7.0-7.2 (m, 5H), 7.4-7.6 (m, 1H).

Workup

  1. additionAfter the addition
  2. waitThe reaction was kept at 0° C. for 1 h
  3. waitat 50° C. for 5 h
  4. temperatureThe reaction was cooled to 0° C
  5. customto quench the reaction
  6. additionfollowed by addition of 2N HCl (8 mL)
  7. extractionThe mixture was extracted with ether (3×20 mL)
  8. dry with materialThe extract was dried over anhydrous Na2SO4
  9. customEvaporation of ether

Sources & evidence

ORD record
ord-d995b0533c7b4ad1837d920ce153283d
Source dataset
uspto-grants-2011_01
Patent number
US07868047B2

Reaction notes

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