Hydrochloric Acid → HCID 86590507, compound

HRID 2416129Notes

Reaction equation

HRID 2416129 reaction equation
[Cl:1][C:2]1[C:3]([Cl:20])=[C:4](Cl)[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:18]=1.[ClH:21]>C(O)C.[Zn]>[Cl:21][C:18]1[C:6]2[CH2:7][C@H:8]([C:15]([OH:17])=[O:16])[C@H:9]([C:11]([F:14])([F:13])[F:12])[O:10][C:5]=2[CH:4]=[C:3]([Cl:20])[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10383075HCID 10383075, compound

Product 1

HCID 86590507HCID 86590507, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A solution of 6,7,8-trichloro-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid (0.28 g, 0.81 mmol, prepared as described in WO98/47890, in ethanol (10 mL) was treated with concentrated HCl (5 mL) and zinc powder (1.21 g, 18.5 mmol). The mixture was stirred at room temperature for 3 hours, filtered, and concentrated in vacuo. The residue was extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo to give a white solid (0.31 g) which was a 3:2 mixture of cis and trans isomers. The isomers were separated by reverse phase HPLC to obtain the desired cis isomer as a white solid (0.11 g, 39%): mp 207.3-208.5° C. 1H NMR (acetone-d6/300 MHz) 7.23 (s, 1H), 5.17-5.31 (m, 1H), 3.58-3.72 (m, 1H), 3.19 (dd, 1H, J=17.9 Hz, 6.5 Hz), 3.10 (dd, 1H, J=17.9 Hz, 7.7 Hz) 19F NMR (acetone-d6/282 MHz) −74.6 (d, J=7.2 Hz). ESHRMS m/z 346.9270 (M−H, Calc'd 346.9256). Anal. Calc'd for C11H6Cl3F3O3: C, 37.80; H, 1.73; Cl, 30.43. Found: C, 37.66; H, 1.75; Cl, 30.71.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e671881ad6c4c168619d13f4a471513
Source dataset
uspto-grants-2004_11
Patent number
US06822102B2

Reaction notes

Loading…