HCID 19815433, compound → HCID 15698115, compound

HRID 653905Notes

Reaction equation

HRID 653905 reaction equation
C([CH:3]([CH:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=O)[CH:4]=[O:5])C>FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>[C:16]([C:6]1[CH:3]=[CH:4][O:5][C:7]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 1

HCID 19815433HCID 19815433, compound

Product 1

HCID 15698115HCID 15698115, compoundYield 119.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalyst2×HCID 9845Trifluoroacetic anhydrideSolvent2×

Procedure

Ethyl 3-Carboethoxy-4-(4-methylphenyl)-4-(oxo)-butanal (10.00 g), trifluoroacetic anhydride (50 mL) and trifluoroacetic acid (2 drops) were mixed and stirred at 0° over ice and allowed to warm to room temperature. After 3 hours, more trifluoroacetic anhydride (50 mL) together with trifluoroacetic acid (2 drops) were added at room temperature. The next day, the solvent was removed in vacuo and the residue partitioned between 1N NaOH (200 mL) and ethyl acetate (200 mL). The layers were separated and the organic layer washed with 1N NaOH (2×200 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield a brown oil (9.95 g) which was flash chromatographed in 99:1 hexane/ethyl acetate to yield 2.57 g of an off-white solid; m.p. 79.0°-80.5°. NMR (200 MHz, CDCl3) δ 7.88 (d, 2H, J=9Hz); 7.42 (d, 1H, J=2Hz); 7.26 (d, 2H, J=9Hz); 6.83 (d, 1H, J=2Hz); 4.34 (q, 2H, J=7Hz); 2.40 (s, 3H); 1.34 (t, 3H, J=7Hz). Anal. Calcd. for C14H14O3 : C, 73.03; H 6.13. Found: C, 73.52; H, 6.30.

Workup

  1. customThe next day, the solvent was removed in vacuo
  2. customthe residue partitioned between 1N NaOH (200 mL) and ethyl acetate (200 mL)
  3. customThe layers were separated
  4. washthe organic layer washed with 1N NaOH (2×200 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-224c79acb8ff44ac816592501879c9af
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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