Trifluoroacetic acid → HCID 22966850, compound

HRID 1266638Notes

Reaction equation

HRID 1266638 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:11][CH:12]([O:31][C:32](=[O:34])[CH3:33])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]2[CH2:28][O:27]C(C)(C)[O:25]2)=[CH:15][CH:14]=1)(=[O:10])[CH3:9]>CO.C(OCC)(=O)C>[C:32]([O:31][CH:12]([O:11][C:8](=[O:10])[CH3:9])[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([OH:25])[CH2:28][OH:27])=[CH:17][CH:18]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18551507HCID 18551507, compound

Product 1

HCID 22966850HCID 22966850, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Trifluoroacetic acid (1.5 ml) was added to a solution of 7 (5.8 g, 15.26 mmol) in 20% aqueous methanol. The solution was stirred for 40 min at room temperature and then diluted with 400 ml of ethyl acetate and washed with 400 ml of 5% sodium bicarbonate solution followed by 400 ml of water. The organic solution was dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography eluting with a gradient of 50% hexane in ethyl acetate to 100% ethyl acetate to 5% methanol in ethyl acetate. The pure product fractions were evaporated affording an oil: 1.1 g (20%) yield; TLC (5% methanol in ethyl acetate), Rf=0.64; 1H NMR (CDCl3) 7.62 (1H, s, acetal CH), 7.44 (2H, d, J=8.7 Hz, aromatic), 6.90 (2H, d, J=8.6 Hz, aromatic), 3.98 (2H, t, J=6.3 Hz, CH2), 3.68 (1H, m, CH), 3.46 (2H, m, CH2), 2.11 (6H, s, Acetyl), 1.82 (2H, m, CH2), 1.55 (4H, m, CH2). Anal. Calcd for C17H24O7: C, 59.99; H, 7.11. Found: C, 60.26; H, 7.08

Workup

  1. washwashed with 400 ml of 5% sodium bicarbonate solution
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 50% hexane in ethyl acetate to 100% ethyl acetate to 5% methanol in ethyl acetate
  6. customThe pure product fractions were evaporated
  7. customaffording an oil
  8. custom1.1 g (20%) yield

Sources & evidence

ORD record
ord-eccf4f641c6042359ce35e010fb93cda
Source dataset
uspto-grants-2003_04
Patent number
US06548652B2

Reaction notes

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