Acetic Acid → HCID 67425784, compound

HRID 2389079Notes

Reaction equation

HRID 2389079 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:30]([F:33])([F:32])[F:31])=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]1([N+:27]([O-])=O)[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[O:21][CH2:20]1)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>[Zn]>[CH2:1]([O:8][C:9]1[C:10]([C:30]([F:31])([F:33])[F:32])=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]1([NH2:27])[CH2:20][O:21][C:22]([CH3:26])([CH3:25])[O:23][CH2:24]1)[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86642889HCID 86642889, compound

Product 1

HCID 67425784HCID 67425784, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
23 °C

Procedure

5-(6-(benzyloxy)-5-(trifluoromethyl)naphthalen-2-yl)-2,2-dimethyl-5-nitro-1,3-dioxinane (2.00 g, 0.00433 mol) was dissolved in acetic acid (20 mL, 0.4 mol), followed by zinc (2.834 g, 0.04334 mol) in small portions at 23° C. The reaction mixture was then allowed to stir at 23° C. for 4 hours. Excess of acetic acid was removed, and the residue was treated with DCM, and filtered. The organic layer was then treated with NaOH (2N, 2 mL), and separated. The organic layer washed with water (30 mL) and brine (30 mL), and then dried over Na2SO4. Removal of the solvent gave a pure product (1.88 g, 100%). MS (ES, M+1): 432.30.

Workup

  1. customExcess of acetic acid was removed
  2. additionthe residue was treated with DCM
  3. filtrationfiltered
  4. additionThe organic layer was then treated with NaOH (2N, 2 mL)
  5. customseparated
  6. washThe organic layer washed with water (30 mL) and brine (30 mL)
  7. dry with materialdried over Na2SO4
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-fb39b7e7bcfb440cb32c0fed48734044
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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