HCID 19801135, compound → HCID 19106962, compound

HRID 1460577Notes

Reaction equation

HRID 1460577 reaction equation
[CH:1]1[C:10]2[C:9]3([C:15]([O:17]CC)=[O:16])[CH2:11][CH:12]=[CH:13][CH2:14][CH:8]3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[O-].[K+]>O1CCCC1.CCCCCCC>[CH:1]1[C:10]2[C:9]3([C:15]([OH:17])=[O:16])[CH2:11][CH:12]=[CH:13][CH2:14][CH:8]3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 19801135HCID 19801135, compoundHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 19106962HCID 19106962, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

To a solution of the product from Example 18 (7.36 g) in tetrahydrofuran (200 ml) was added potassium trimethylsilanolate (5.30 g). The solution was refluxed for 7 hours then diluted with heptane and filtered. The precipitated solid was dissolved in water/ethyl acetate and acidified with dilute hydrochloric acid. The organic phase was washed with water then extracted with dilute sodium hydroxide (x2). The aqueous layer was washed with ethyl acetate then layered with fresh ethyl acetate and acidified. The solution was washed with water and dried (Na2SO4) and evaporated to a oil which was triturated with ethyl acetate/heptane to give the title compound as a cream colored solid (4.5 g), mp 152°-155° C. and a darker colored second crop (1.7 g) combined yield 94%.

Workup

  1. temperatureThe solution was refluxed for 7 hours
  2. filtrationfiltered
  3. dissolutionThe precipitated solid was dissolved in water/ethyl acetate
  4. washThe organic phase was washed with water
  5. extractionthen extracted with dilute sodium hydroxide (x2)
  6. washThe aqueous layer was washed with ethyl acetate
  7. washThe solution was washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated to a oil which
  10. customwas triturated with ethyl acetate/heptane

Sources & evidence

ORD record
ord-b9d30e5c9345492b97057daad7760cfe
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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