2-Benzofurancarboxaldehyde → HCID 65816420, compound

HRID 1186366Notes

Reaction equation

HRID 1186366 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=[O:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:30][C:31]([Si](C)(C)C)([F:33])[F:32]>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([OH:11])[C:31]([F:33])([F:32])[F:30]

Participants

5

Reactant 3

HCID 613412-BenzofurancarboxaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 65816420HCID 65816420, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of benzofuran-2-carbaldehyde (300 mg, 2.05 mmol) dissolved in tetrahydrofuran (6 mL), a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (1.03 mL, 1.03 mmol) and (trifluoromethyl)trimethylsilane (0.516 mL, 3.49 mmol), the mixture was stirred and reacted at room temperature for 5 hours. Then, purification by preparative thin-layer chromatography (chloroform/methanol=100/1) was performed to give 1-(benzofuran-2-yl)-2,2,2-trifluoroethanol (Compound DR) (194 mg, yield: 44%).

Workup

  1. customreacted at room temperature for 5 hours
  2. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-22b7e932b1844c65bcb2bf7ed6e93a8c
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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