Methanol → 11,11-Diphenyl-11-methoxyundec-1-ene

HRID 275465Notes

Reaction equation

HRID 275465 reaction equation
[H-].[Na+].CO.[C:5]1([C:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([OH:22])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:29]OS(OC)(=O)=O>C1COCC1>[C:23]1([C:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)([O:22][CH3:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 200883261,1-Diphenyl-10-undecen-1-ol

Product 1

HCID 2008832511,11-Diphenyl-11-methoxyundec-1-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.2 g of sodium hydride and 0.1 mL of methanol in 50 mL of THF was added a solution of 10 g of 1,1-diphenyl-10-undecen-1-ol in 20 mL of THF over 2 hrs. The mixture was stirred at room temperature for 4 hrs, then 3.5 mL of dimethylsulfate was added. The mixture was stirred for an additional 75 hrs, then 2 mL of methanol was added to quench any excess sodium hydride. The solvent was distilled in vacuo, the residue taken up in ether, and the solution washed with 10% by wt of hydrochloric acid, water, and saturated sodium hydrogen carbonate. The solution was then dried with sodium sulfate and concentrated in vacuo to give 10.6 g of 11,11-diphenyl-11-methoxyundec-1-ene which is characterized by:

Workup

  1. stirringThe mixture was stirred for an additional 75 hrs
  2. customto quench any excess sodium hydride
  3. distillationThe solvent was distilled in vacuo
  4. washthe solution washed with 10% by wt of hydrochloric acid, water, and saturated sodium hydrogen carbonate
  5. dry with materialThe solution was then dried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aacae9c137504bb6b2733f63487142c0
Source dataset
uspto-grants-1995_02
Patent number
US05393795

Reaction notes

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