Hexane → HCID 21883544, compound

HRID 722388Notes

Reaction equation

HRID 722388 reaction equation
C([O:3][C:4]([C:6]1[CH:7]([C:19]([F:22])([F:21])[F:20])[O:8][C:9]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=2[C:11]=1[CH2:12][CH3:13])=[O:5])C.[OH-].[Na+].CCCCCC>C1COCC1.C(O)C.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:9]2[O:8][CH:7]([C:19]([F:21])([F:20])[F:22])[C:6]([C:4]([OH:5])=[O:3])=[C:11]([CH2:12][CH3:13])[C:10]=2[CH:14]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 14798Sodium HydroxideHCID 21883572HCID 21883572, compound

Product 1

HCID 21883544HCID 21883544, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

The ester from Step 1 (0.282 g, 0.842 mmol) was dissolved in a THF-EtOH—H2O mixture (10 mL, 7:2:1). The resulting solution was treated with aqueous sodium hydroxide (0.340 mL, 0.842 mmol of a 2.5 N solution) and was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was dissolved in water 10 mL). Diethyl ether (10 ml ) was added and the resulting mixture acidified by the addition of a few drops of concentrated HCl. The diethyl ether layer was separated, and the aqueous phase was extracted with additional ether(2×10 mL). The ether extracts were combined, dried over MgSO4, filtered, and evaporated to yield a clear oil. Addition of hexane (10 mL) resulted in the formation of a white precipitate which was collected by vacuum filtration to afford the title compound (0.064 g, 25%) as a white powder: mp 170.9–172.1° C. 1H NMR (CDCl3/300 MHz) 7.47 (d, 1H, J=2.4 Hz), 7.30 (dd, 1H, J=2.4, 8.7 Hz), 6.96 (d, 1H, J=8.7 Hz), 5.76 (q, 1H, J=7.0 Hz), 3.08 (q, 2H, J=7.6 Hz), 1.27 (t, 3H, J=7.5 Hz). FABLRMS m/z 305.2 (M−H).ESHRMS m/z 305.0185 (M−H, Calc'd. 305.0192). Anal. Calc'd for C13H8ClF3O3: C, 50.92; H, 3.29; Cl, 11.56. Found: C, 50.68; H, 3.18; Cl, 11.64.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water 10 mL)
  3. additionDiethyl ether (10 ml ) was added
  4. additionthe resulting mixture acidified by the addition of a few drops of concentrated HCl
  5. customThe diethyl ether layer was separated
  6. extractionthe aqueous phase was extracted with additional ether(2×10 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto yield a clear oil
  11. customresulted in the formation of a white precipitate which
  12. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-4d72e73fc6a748b695e3b8552cc1f4c0
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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