Methyl triflate → HCID 59283877, compound

HRID 1642002Notes

Reaction equation

HRID 1642002 reaction equation
[Si]([O:8][C:9]1[C:18]([CH3:19])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:20][CH2:21][OH:22])(C(C)(C)C)(C)C.[C:23](=O)(O)[O-].[Na+].O(C)S(C(F)(F)F)(=O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.C(OCC)(=O)C>[OH:8][C:9]1[C:18]([CH3:19])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:20][CH2:21][O:22][CH3:23]

Participants

7

Reactant 4

HCID 9526Methyl triflateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 59283874HCID 59283874, compound

Product 1

HCID 59283877HCID 59283877, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-(tert-butyldimethylsilyloxy)-3-(2-hydroxyethyl)-5-methylbenzoate (48 mg, 0.148 mmol) in dichloromethane (3 mL) was treated with sodium bicarbonate (60 mg, 4 equivalents) and methyl triflate (68 uL, 4 equivalents). the reaction was stirred at room temperature for 16 h by which time TLC analysis indicated ˜50% conversion. The reaction was then diluted with ethyl acetate (20 mL) and filtered. The filtrate was evaporated to dryness. The residue was dissolved in THF (5 mL) and tetrabutylammonium fluoride (60 mg, 1.5 equivalents) was added. The reaction was stirred at room temperature. after 5 minutes, TLC analysis indicated complete conversion. The solvent was removed under educed pressure and the residue was dissolved in ethyl acetate (1 mL) and purified by preparative TLC on silica using 25% ethyl acetate/hexanes. Yield=13 mg (40%).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in THF (5 mL)
  4. stirringThe reaction was stirred at room temperature
  5. waitafter 5 minutes
  6. customThe solvent was removed
  7. dissolutionthe residue was dissolved in ethyl acetate (1 mL)
  8. custompurified by preparative TLC on silica using 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-db3d25ebc10f44139f1fbb1a774f794d
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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