Tetrahydrofuran → HCID 86689892, compound

HRID 536158Notes

Reaction equation

HRID 536158 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]#N)=[N:13][CH:14]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].CC(C[AlH]CC(C)C)C.[O:30]1CCCC1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH:15]=[O:30])=[N:13][CH:14]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 66826128HCID 66826128, compound

Product 1

HCID 86689892HCID 86689892, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-2-pyridinecarbonitrile (0.876 g, 2.93 mmol) in anhydrous tetrahydrofuran (30 mL), was added DIBAL-H (5.87 mL, 5.87 mmol) dropwise at −78° C. The reaction mixture was stirred for 1 h at −78° C., then quenched with 1N HCl solution, concentrated. Purification via ISCO afforded the title product (350 mg) as an off white solid. LC-MS (ESI): m/z 302 [M+H]+; 3.47 min (ret time).

Workup

  1. customquenched with 1N HCl solution
  2. concentrationconcentrated
  3. customPurification via ISCO

Sources & evidence

ORD record
ord-a05c4641815746f2a07254b0e2546c8a
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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