HCID 68380040, compound → HCID 68380044, compound

HRID 2178669Notes

Reaction equation

HRID 2178669 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[CH:16]1[CH2:19][C:18](=[O:20])[C:17]1(Cl)Cl)[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[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[CH:16]1[CH2:19][C:18](=[O:20])[CH2:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68380040HCID 68380040, compound

Product 1

HCID 68380044HCID 68380044, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-[2-(benzyloxy)-5-fluorophenyl]-2,2-dichlorocyclobutanone (C18) (1.4 g, 4.14 mmol) and zinc dust (1.08 g, 16.5 mmol) in acetic acid (25 mL) was stirred at room temperature for 2 hours and then at 100° C. for 1.25 hours. The mixture was filtered through Celite, and the filtrate was washed with water (50 mL) and saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% ethyl acetate in heptanes) afforded the title compound as a colorless oil. Yield: 674 mg, 2.49 mmol, 60%. LCMS m/z 179.4 [M−(C7H7)]. 1H NMR (400 MHz, CDCl3) δ 3.22-3.31 (m, 2H), 3.36-3.46 (m, 2H), 3.75-3.85 (m, 1H), 5.08 (s, 2H), 6.87-6.95 (m, 2H), 6.99 (dd, J=9.2, 2.7 Hz, 1H), 7.33-7.44 (m, 5H).

Workup

  1. waitat 100° C. for 1.25 hours
  2. filtrationThe mixture was filtered through Celite
  3. washthe filtrate was washed with water (50 mL) and saturated aqueous sodium chloride solution (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (Gradient: 0% to 30% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-2884bfb76a6f4e6d91840bc21013d1cf
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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