Trifluoroacetic acid → {4-[(1,1-Dimethylethyl)thio]-5-hydroxy-2-pyridinyl}methyl acetate

HRID 639036Notes

Reaction equation

HRID 639036 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([S:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([O:17]CC2C=CC(OC)=CC=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([S:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([OH:17])=[CH:8][N:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68576335HCID 68576335, compound

Product 1

HCID 68577438{4-[(1,1-Dimethylethyl)thio]-5-hydroxy-2-pyridinyl}methyl acetateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [4-[(1,1-dimethylethyl)thio]-5-({[4-(methoxy)phenyl]methyl}oxy)-2-pyridinyl]methyl acetate (9 g, 24 mmol) in dichloromethane (100 mL) was treated with triethylsilane (3.86 mL, 24 mmol). The reaction mixture was stirred for 10 minutes before adding trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature for 3 hours under argon atmosphere. The solvents were evaporated under vacuum. The residue was taken up in dichloromethane and chromatographed on silica gel eluting with 10%-30% ethyl acetate in hexane to afford the product as an oil (5.1 g, 83%); MS (+ve ion electrospray) m/z 256 (MH+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours under argon atmosphere
  2. customThe solvents were evaporated under vacuum
  3. customchromatographed on silica gel eluting with 10%-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f803601791a347b5a3a5036e038cde2e
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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