Water → HCID 86639423, compound

HRID 1690189Notes

Reaction equation

HRID 1690189 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:28][CH2:29][O:30][CH3:31])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[CH2:32][CH2:33][CH3:34])=[CH:8][C:5]=1[C:6]#[N:7].B(F)(F)F.CCOCC.C([BH3-])#N.[Na+].O>O1CCCC1>[OH:1][CH2:3][CH2:2][C:4]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:28][CH2:29][O:30][CH3:31])([C:24]([F:25])([F:26])[F:27])[C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[CH2:32][CH2:33][CH3:34])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherate2×HCID 5003444Sodium cyanoborohydride2×HCID 86639421HCID 86639421, compound

Product 1

HCID 86639423HCID 86639423, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-oxiranyl-5-[2-propyl-4-(2,2,2-trifluoro-1-methoxymethoxy-1-trifluoromethyl-ethyl)-phenoxy]-benzonitrile (5.0 mg, 0.0102 mmol) in tetrahydrofuran (200 μL) was sequentially added with boron trifluoride diethyl ether (2.5 μL, 0.0204 mmol) and sodium cyanoborohydride (2.6 mg, 0.0409 mmol) under ice-cold conditions, and stirred at room temperature for 2 hours. Subsequently, the resultant mixture was further sequentially added with boron trifluoride diethyl ether (2.5 μL, 0.0204 mmol) and sodium cyanoborohydride (2.6 mg, 0.0409 mmol) under ice-cold conditions, and stirred at room temperature overnight. After completion of the reaction, the reaction solution was added with water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane/ethyl acetate), and 2-(2-hydroxy-ethyl)-5-[2-propyl-4-(2,2,2-trifluoro-1-methoxymethoxy-1-trifluoromethyl-ethyl)-phenoxy]-benzonitrile (2.2 mg, yield 44%) was obtained as a yellow oil.

Workup

  1. stirringstirred at room temperature overnight
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-9abb4849646f44db9ea0419c7d3d6a3a
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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