Potassium Hydroxide → HCID 67425110, compound

HRID 918990Notes

Reaction equation

HRID 918990 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20][C:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36].[OH-:37].[K+]>C(#N)C.CCOC(C)=O>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20][C:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24412Potassium PersulfateHCID 67424227HCID 67424227, compound

Product 1

HCID 67425110HCID 67425110, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

RuCl3 (10 mg) and potassium persulphate (2.8 g, 10.2 mmol) were added to a solution of 16-(tetrahydro-2H-pyran-2-yloxy)hexadec-14-yn-1-ol (1.2 g, 3.55 mmol) in acetonitrile (20 mL). After 10 min, KOH (30 mL of a 2 M soln) was added. After an additional 3 h, the reaction mixture was neutralized to pH 7, diluted with EtOAc (100 mL), and washed with water (3×75 mL). The combined aqueous extracts were back-extracted with EtOAc (3×75 mL). All of the organic extracts were combined, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by SiO2 column chromotography using 20% EtOAc/hexanes as eluent to give 16-(tetrahydro-2H-pyran-2-yloxy)hexadec-14-ynoic acid (1.05 g, 91%) as a colorless oil that was used without further purification. TLC: 50% EtOAc/hexanes, Rf≈0.35. Lit. ref.: R. S. Varma; M. Hogan Tetrahedron Lett. 1992: 33, 719.

Workup

  1. waitAfter an additional 3 h
  2. washwashed with water (3×75 mL)
  3. extractionThe combined aqueous extracts were back-extracted with EtOAc (3×75 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by SiO2 column chromotography

Sources & evidence

ORD record
ord-b502e16b26644288a8a5e9de3e8cd1a4
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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