Triethylamine → HCID 15550250, compound

HRID 1595046Notes

Reaction equation

HRID 1595046 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.O([Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])S(C(F)(F)F)(=O)=O>CN(C=O)C>[CH:33]([Si:32]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1)([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 102201704-[Benzo(b)thiophen-2-yl]phenol

Product 1

HCID 15550250HCID 15550250, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-hydroxyphenyl)benzothiophene (2.84 g, 12.6 mmol), triethylamine (2.5 g, 25.2 mmol) and 30 mL dry DMF was cooled in an ice bath and treated with triisopropylsilyl triflate (7.7 g, 25.2 mmol). The reaction was allowed to warm to room temperature, quenched with 100 mL brine then extracted twice with 50 mL EtOAc. The combined extract was washed with brine, dried over MgSO4 and concentrated to dryness. The resulting solid was purified by chromatrography (SiO2, 5% EtOAc in Hexanes) to yield 4.7 g (12.3 mmol, 98%) of a solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. customquenched with 100 mL brine
  3. extractionthen extracted twice with 50 mL EtOAc
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe resulting solid was purified by chromatrography (SiO2, 5% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-352571e1bfc944eaa5414e1051082582
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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