1-(6-(Trifluoromethyl)pyridine-3-yl)propan-1-ol → HCID 69404393, compound

HRID 241448

Reaction equation

HRID 241448 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1>C(Cl)Cl>[F:13][C:2]([F:1])([F:14])[C:3]1[N:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 682190391-(6-(Trifluoromethyl)pyridine-3-yl)propan-1-ol

Product 1

HCID 69404393HCID 69404393, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 1-[6-(trifluoromethyl)-3-pyridyl]propan-1-ol (2.010 g, 9.796 mmol) in DCM (40 mL). Add 3,3,3-Triacetoxy-3-iodophthalide (4.712 g, 10.776 mmol), and stir for 16 hours. Dilute with DCM (100 mL). Wash with 0.5 N NaOH (100 mL). Dry the organic extracts over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the title compound (1.910 g, 96% yield) as a white solid. 1H NMR (400.43 MHz, d6-DMSO) δ 9.21 (dd, J=0.5, 1.4 Hz, 1H), 8.51-8.49 (m, 1H), 8.03 (dd, J=0.7, 8.1 Hz, 1H), 3.12 (q, J=7.1 Hz, 2H), 1.05 (t, J=7.1 Hz, 3H).

Workup

  1. washWash with 0.5 N NaOH (100 mL)
  2. dry with materialDry the organic extracts over Na2SO4
  3. filtrationfilter
  4. customcollect the filtrate
  5. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-0e28d9724a5e4e639e196f9618e75d76
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Linked notes

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