HCID 16107468, compound → HCID 16107461, compound

HRID 556215Notes

Reaction equation

HRID 556215 reaction equation
[N:1]([CH2:4][C:5]([CH2:23][O:24][C:25]([C:34]([F:37])([F:36])[F:35])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])([CH2:8][O:9][C:10]([C:19]([F:22])([F:21])[F:20])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])[CH2:6][OH:7])=[N+:2]=[N-:3].CC(C)=[O:40].OS(O)(=O)=O.O=[Cr](=O)=O>CC(O)C>[N:1]([CH2:4][C:5]([CH2:8][O:9][C:10]([C:11]([F:14])([F:13])[F:12])([C:15]([F:18])([F:17])[F:16])[C:19]([F:21])([F:22])[F:20])([CH2:23][O:24][C:25]([C:30]([F:31])([F:32])[F:33])([C:26]([F:27])([F:28])[F:29])[C:34]([F:35])([F:36])[F:37])[C:6]([OH:40])=[O:7])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 16107468HCID 16107468, compoundHCID 131709961Jones' reagent

Product 1

HCID 16107461HCID 16107461, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of alcohol 11 (19.0 g, 31.8 mmol) at 0° C. was added dropwise a solution of Jones reagent (2.7 N, 31 mL). After addition, the reaction mixture was stirred at room temperature for 1 hour and 2-propanol (10 mL) was slowly added. The solvent was removed under vacuo and the residue was dissolved in ether. Washing the ether solution with water, separation the layers and the aqueous lay was extracted with ether. The combined organic lay was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give the acid 12 as a solid (18.5 g, 95%). mp. 97-98° C.; 1H NMR (400 MHz, CD3OD) δ 3.62 (s, 2H), 4.25 (d, J=8.8 Hz, 2H), 4.33 (d, J=8.4 Hz, 2H); 19F NMR (376 MHz, CD3OD) δ −71.16 (s); 13C NMR (100.7 MHz, CD3OD) δ 50.9, 53.6, 67.5, 81.2 (m), 121.6 (q, J=292.6 Hz), 171.9; MS (CI) m/z 612 (M++1, 100), 584 (80); HRMS (CI) Calcd for C13H8F18N3O4: 612.0227, Found: 612.0204.

Workup

  1. additionAfter addition
  2. customThe solvent was removed under vacuo
  3. dissolutionthe residue was dissolved in ether
  4. washWashing the ether solution
  5. customwith water, separation the layers
  6. extractionthe aqueous lay was extracted with ether
  7. dry with materialThe combined organic lay was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2b27d9f03dbb42d89abc5fa8cb39af7d
Source dataset
uspto-grants-2011_11
Patent number
US08052961B2

Reaction notes

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