Triethylsilane → HCID 18467896, compound

HRID 2229477Notes

Reaction equation

HRID 2229477 reaction equation
C(O[CH:5]1[CH2:9][O:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6]1)(C)C.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[C:15]1([C:7]2([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5][CH2:9][O:8]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 18467885HCID 18467885, compound

Product 1

HCID 18467896HCID 18467896, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-isopropoxy-2-phenyl-2-tetrahydrofuroic acid, ethyl ester (189 mg, 0.68 mmol) in 4 ml of TFA was added triethylsilane (395 mg, 3.40 mmol). After heating at 70° C. for 4 h, the reaction mixture was poured into NaHCO3 (saturated) and extracted with ethyl acetate. The extracts were washed with brine and dried over MgSO4, filtered, and concentrated. The residue was purified by preparative TLC eluting with ethyl acetate/hexane=5:95 to give ethyl 2-phenyl-2-tetrahydrofuroate (170 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC
  7. washeluting with ethyl acetate/hexane=5:95

Sources & evidence

ORD record
ord-fcaea611d0264480a93c00a12c72869a
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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