Triethylsilane → HCID 12508514, compound

HRID 2081808Notes

Reaction equation

HRID 2081808 reaction equation
FC(F)(F)S(O)(=O)=O.[OH:9][C:10]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:11]=1[C:12]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=O.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[OH:9][C:10]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:11]=1[CH2:12][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 12052Triethylsilane2×HCID 62406Trifluoromethanesulfonic acid2×HCID 516892Sodium BicarbonateHCID 19780688HCID 19780688, compound2×

Product 1

HCID 12508514HCID 12508514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent5×

Procedure

Trifluoromethanesulphonic acid (0.2 ml, 2.3 mM) in dichloromethane (0.5 ml) was added dropwise to a solution of the epsilon-lactone of 3-(2-hydroxy-4,6-dimethylbenzoyl)propionic acid, [m.p. 77° C.; prepared by the method described in Acta. Chem. Scand. 1972, 26, 2372, but starting from 3-(2-hydroxy-4,6-dimethylbenzoyl)propionic acid, itself prepared as described in Liebigs Ann. Chem. 1985, 560] in dichloromethane (1 ml) at 0° C. under argon, followed by a solution of triethylsilane (200 mg, 1.7 mM) in dichloromethane (0.5 ml). After 5 minutes, a further portion of trifluoromethanesulphonic acid (0.2 ml, 2.3 mM) in dichloromethane (0.5 ml) was added followed by triethylsilane (200 mg; 1.7 mM) in dichloromethane (0.5 ml). The reaction mixture was stirred for 2 hours at ambient temperature, then poured into saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The combined extracts were washed with brine, dried (Na2SO4), and the solvent was removed by evaporation. The residual oil was purified by flash chromatography, eluting with hexane/dichloromethane (1:1 v/v increasing in polarity to 1:3 v/v), giving the epsilon-lactone of 4-(2-hydroxy-4,6-dimethylphenyl)butyric acid (C) as a colourless oil; NMR: 2.10(2H,tt), 2.29(6H,s), 2.43(2H,t), 2.79(2H,t), 6.75(1H,s), 6.86(1H,s); I.R (thin film) 1720 cm-1.

Workup

  1. customprepared by the method
  2. customprepared
  3. customat 0° C.
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed by evaporation
  8. customThe residual oil was purified by flash chromatography
  9. washeluting with hexane/dichloromethane (1:1 v/v increasing in polarity to 1:3 v/v)

Sources & evidence

ORD record
ord-1e1f5505f61740d1a78309d523b16467
Source dataset
uspto-grants-1993_02
Patent number
US05185452

Reaction notes

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