Triethylsilane → HCID 70201455, compound

HRID 342461Notes

Reaction equation

HRID 342461 reaction equation
C1([C:7]2[C:8]3[C:16](CO)=[CH:15][CH:14]=[C:13]([NH:19][C:20](=[O:29])[C:21]4[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:28])[C:9]=3[O:10][C:11]=2[CH3:12])CCCCC1.C([SiH]([CH2:35][CH3:36])CC)C>FC(F)(F)C(O)=O>[CH:35]1([CH2:36][C:7]2[C:8]3[CH:16]=[CH:15][CH:14]=[C:13]([NH:19][C:20](=[O:29])[C:21]4[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:28])[C:9]=3[O:10][C:11]=2[CH3:12])[CH2:9][CH2:8][CH2:7][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 70198692HCID 70198692, compound

Product 1

HCID 70201455HCID 70201455, compoundYield 134.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 3-(1-cyclohexyl)hydroxymethyl-7-(2,6-dichlorobenzoylamino)-2-methylbenzo[b]furan (65 mg) and triethylsilane (87 mg) in trifluoroacetic acid (3 ml) was stirred at ambient temperature for overnight. The reaction mixture was concentrated in vacuo. To the residue was added aqueous saturated sodium bicarbonate and the separated oil was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from hexane to give 3-cyclohexylmethyl-7-(2,6-dichlorobenzoylamino)-2-methylbenzo[b]furan (42 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the residue was added aqueous saturated sodium bicarbonate
  3. extractionthe separated oil was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel
  8. customthe obtained oil was crystallized from hexane

Sources & evidence

ORD record
ord-a0ac621cea794a22b2e6819766010e9d
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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