Triethylsilane → HCID 67459678, compound

HRID 554540Notes

Reaction equation

HRID 554540 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[S:11][C:10]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[S:11][C:10]=1[CH2:18][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12052Triethylsilane2×HCID 67461036HCID 67461036, compound

Product 1

HCID 67459678HCID 67459678, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (3-benzyloxy-5-trifluoromethylthiophen-2-yl)-(4-methoxy-phenyl)methanone (220.2 mg, 0.56 mmol) as synthesized by the method described in International Publication No. WO04/007517 and triethylsilane (1.34 mL, 8.41 mmol) in dichloromethane (1.1 mL), trifluoroacetic acid (3 mL) was added at 0° C. in a nitrogen stream over five minutes. The reaction mixture was stirred at the same temperature for 6.75 hours, and then triethylsilane (0.9 mL, 5.61 mmol) was added thereto. The reaction mixture was stirred at the same temperature for 16.75 hours, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (108.8 mg, 51%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 16.75 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)]

Sources & evidence

ORD record
ord-77bffb92e0ad4e04806a45e38d0b3b33
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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