Isopropanol → 7-Acetoxy-hept-5-ynoic acid

HRID 2364894Notes

Reaction equation

HRID 2364894 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][O:14][C:15](=[O:17])[CH3:16])(C)(C)C.CC(C)=[O:22].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[C:15]([O:14][CH2:13][C:12]#[C:11][CH2:10][CH2:9][CH2:8][C:7]([OH:6])=[O:22])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 3776Isopropanol2×HCID 86593935Acetic acid 7-(tert-butyl-dimethyl-silanyloxy)-hept-2-ynyl esterHCID 131709961Jones' reagent

Product 1

HCID 219644197-Acetoxy-hept-5-ynoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of crude (28) in acetone (100 mL) was treated with Jones Reagent (18.0 mL, 41.4 mmol, 2.3 M) and cooled with an ice bath. After 1 hour at room temperature, 10 mL isopropyl alcohol was added and the mixture stirred for 15 minutes. The mixture still had a brown color so another 10 mL isopropyl alcohol was added. After another 15 minutes, the color had not changed so the mixture was filtered through celite and the filtrate evaporated in vacuo. The residue was partitioned between 100 mL ether and 100 mL saturated ammonium chloride solution. The aqueous layer was extracted with 100 mL ether and the combined ether solution washed with brine and then dried (MgSO4), filtered and evaporated to leave a yellow oil (6.333 g) that was used directly in the next step.

Workup

  1. temperaturecooled with an ice bath
  2. additionwas added
  3. waitAfter another 15 minutes
  4. filtrationwas filtered through celite
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was partitioned between 100 mL ether and 100 mL saturated ammonium chloride solution
  7. extractionThe aqueous layer was extracted with 100 mL ether
  8. washthe combined ether solution washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-f17cf9ca501c4f3a850f03345045e6b7
Source dataset
uspto-grants-2014_04
Patent number
US08697057B2

Reaction notes

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