Hexane → HCID 69055523, compound

HRID 2100575Notes

Reaction equation

HRID 2100575 reaction equation
CCCCCC.[H-].[Na+].COP([CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(OC)=O.[CH:26]([C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[C:29]=1[C:30]([O:32][CH3:33])=[O:31])=O>C1COCC1>[CH2:19]([O:18][C:16](=[O:17])/[CH:15]=[CH:26]/[C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:39])([F:40])[F:41])[C:29]=1[C:30]([O:32][CH3:33])=[O:31])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 2773759Benzyl DimethylphosphonoacetateHCID 86090086HCID 86090086, compound

Product 1

HCID 69055523HCID 69055523, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of hexane-washed sodium hydride (0.42 g of 60% suspension in mineral oil, 10.52 mmol) in 120 mL of THF at 0° C. was added benzyl 2-(dimethoxyphosphoryl)acetate (2.72 g, 10.52 mmol) dropwise in 10 mL of THF. The resulting mixture was stirred 5 min at 0° C. and then was allowed to warm to ambient temperature and stirred for 20 min. To this solution was added methyl 2-formyl-6-(trifluoromethyl)benzoate (2.22 g, 9.56 mmol) dropwise in 10 mL of THF. The resulting solution was stirred at ambient temperature for 1 h. The reaction mixture was quenched with 1N HCl (100 mL) and extracted with ethyl acetate. The organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 3.4 g (97%) of the title compound which was sufficiently pure to be used without purification. 1H NMR (CDCl3): δ 7.79 (d, 1H, J=7.9 Hz), 7.72-7.67 (m, 2H), 7.55 (t, 1H, J=7.9 Hz), 7.38-7.30 (m, 5H), 6.47 (d, 1H, J=15.8 Hz), 5.23 (s, 2H), 3.94 (s, 3H). LRMS (ESI): 387.17 (M+H+Na)+.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 20 min
  3. stirringThe resulting solution was stirred at ambient temperature for 1 h
  4. customThe reaction mixture was quenched with 1N HCl (100 mL)
  5. extractionextracted with ethyl acetate
  6. washThe organics were washed with sat'd aq NaHCO3 and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered through a pad of silica gel
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-944e7639aaad40a98363f692d256c5f8
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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