2-(Benzyloxy) ethanol → HCID 23336639, compound

HRID 903553Notes

Reaction equation

HRID 903553 reaction equation
Cl[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[CH3:18][N:19]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]1.[CH2:25]([O:32][CH2:33][CH2:34][OH:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>N1C=CC=CC=1>[CH3:18][N:19]1[CH2:23][CH2:22][CH:21]([O:24][C:3](=[O:4])[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:35][CH2:34][CH2:33][O:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20]1

Participants

5

Reactant 3

HCID 121412-(Benzyloxy) ethanolHCID 179412902-98-9HCID 930741-Methyl-3-pyrrolidinol

Product 1

HCID 23336639HCID 23336639, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of chlorodiphenylacetyl chloride (20 g), 1-methyl-3-pyrrolidinol (7.6 g), and pyridine (35 g) is kept at room temperature for two hours. After adding 45 g of 2-benzyloxyethanol, the mixture is refluxed gently for 18 hours. Excess pyridine and benzyloxyethanol are distilled off under reduced pressure, the residue is dissolved in ether and washed twice with water. The organic phase is dried over magnesium sulfate (MgSO4), filtered and the filtrate evaporated to dryness. Chromatography of the residue on the silica gel with ethyl acetate-hexane-triethylamine (50:50:1) as eluent affords 18 g of 1-methyl-3-[2,2-diphenyl-2-(2-benzyloxyethoxy)acetoxy]pyrrolidine as an oil.

Workup

  1. temperaturethe mixture is refluxed gently for 18 hours
  2. distillationExcess pyridine and benzyloxyethanol are distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in ether
  4. washwashed twice with water
  5. dry with materialThe organic phase is dried over magnesium sulfate (MgSO4)
  6. filtrationfiltered
  7. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-76dd6a197ada47d181bfacd248bb8645
Source dataset
uspto-grants-1980_10
Patent number
US04228171

Reaction notes

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