Triethylsilane → HCID 57043096, compound

HRID 1728984Notes

Reaction equation

HRID 1728984 reaction equation
[C:1]([C@@H:9]1[CH2:14][CH:13]=[CH:12][CH2:11][C@@H:10]1[C:15]([O:17][CH3:18])=[O:16])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH3:18][O:17][C:15]([C@@H:10]1[C@@H:9]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH2:12][CH2:11]1)=[O:16]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 57307440HCID 57307440, compound

Product 1

HCID 57043096HCID 57043096, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

438 mg of (1S, 2R)-2-benzoyl-1-methoxycarbonylcyclohex-4-ene was dissolved in 2.5 ml of trifluoroacetic acid. To the solution, 2.5 ml of triethylsilyl hydride (Et3SiH) was added at 50° C., and the solution was stirred for 30 minutes at the same temperature. After the solution was allowed to stand to return to room temperature, a saturated sodium bicarbonate solution was added, and the water layer was extracted with ether. Then, the organic layer was dried over anhydrous magnesium sulfate, concentrated, and the residure was subjected to silica gel column chromatography (ether:hexane=4:96), thereby obtaining 221 mg of the titled compound.

Workup

  1. customto return to room temperature
  2. extractionthe water layer was extracted with ether
  3. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f0d75c64daa40738cf73542c61644b9
Source dataset
uspto-grants-1994_07
Patent number
US05329042

Reaction notes

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