Potassium Acetate → HCID 91692565, compound

HRID 2183423Notes

Reaction equation

HRID 2183423 reaction equation
[CH3:1][CH2:2][C@@H:3]([CH:28]([CH3:30])[CH3:29])/[CH:4]=[CH:5]/[C@H:6]([C@@H:8]1[C@@:12]2([CH3:27])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@H:23]([OH:25])[CH2:24][C:19]4=[CH:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH3:7].S([C:35]1C=CC(C)=CC=1)([O-])(=O)=O.C([O-])(=O)C.[K+]>CO>[CH3:1][CH2:2][C@H:3]([CH:28]([CH3:29])[CH3:30])/[CH:4]=[CH:5]/[C@H:6]([C@@H:8]1[C@@:12]2([CH3:27])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][CH:23]([O:25][CH3:35])[CH2:24][C:19]4=[CH:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH3:7]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 86659246HCID 86659246, compound

Product 1

HCID 91692565HCID 91692565, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of stigmasterol tosylate (2) (64 g, 112.9 mmol) and potassium acetate (70 g, 713.19 mmol) in anhydrous methanol (1500 mL) was refluxed for 4.5 h under argon atmosphere. The methanol was evaporated in vacuo, and then ether (2 L) was added, washed with water (500 mL), 5% NaHCO3 (2×400 mL) and brine (400 mL) and dried (MgSO4). The solvent was evaporated in vacuo to afford 47 g (92%) of stigmasterol methyl ether (3) as a pale yellow viscous liquid.

Workup

  1. temperaturewas refluxed for 4.5 h under argon atmosphere
  2. customThe methanol was evaporated in vacuo
  3. additionether (2 L) was added
  4. washwashed with water (500 mL), 5% NaHCO3 (2×400 mL) and brine (400 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-aa78065c99834cb98a4acadb121790a7
Source dataset
uspto-grants-2005_05
Patent number
US06900191B1

Reaction notes

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