Acetonitrile → 3-[2-(4-{2-Phenoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidine-3-ol

HRID 580963Notes

Reaction equation

HRID 580963 reaction equation
Br[C:2]1[CH:18]=[C:17]([CH3:19])[C:5]([O:6][CH:7](O)[CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:20])[CH:3]=1.Br[C:22]1[CH:32]=[C:31]([CH3:33])[C:25]([O:26]CCOC)=[C:24]([CH3:34])C=1.[C:35](#[N:37])C.Cl[CH2:39]Cl>[OH-].[Na+]>[O:9]([CH2:8][CH2:7][O:6][C:5]1[C:17]([CH3:19])=[CH:18][C:2]([C:34]#[C:24][C:25]2([OH:26])[CH:31]3[CH2:32][CH2:22][N:37]([CH2:35][CH2:33]3)[CH2:39]2)=[CH:3][C:4]=1[CH3:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 540085841-(4-Bromo-2,6-dimethylphenoxy)-2-phenoxyethanolHCID 541527811-(4-Bromo-2,6-dimethylphenoxy)-2-methoxyethane

Product 1

HCID 867541613-[2-(4-{2-Phenoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidine-3-olYield 28%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Using a similar procedure to that described in Example 10, but using 1-(4-bromo-2,6-dimethylphenoxy)-2-phenoxyethanol as starting material in place of 1-(4-bromo-2,6-dimethylphenoxy)-2-methoxyethane and extracting the aqueous mixture obtained after diluting the reaction mixture with 2M aqueous sodium hydroxide with dichloromethane instead of diethyl ether, there was obtained 3-[2-(4-{2-phenoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidine-3-ol (28% yield) as a solid, m.p. 141-142° C. (after recrystallisation from acetonitrile); microanalysis, found: C, 76.2; H, 7.4; N, 3.5%; C25H29NO3 requires: C, 76.7, H, 7.5; N, 3.6%; in 28% yield NMR ([CD3 ]2O): 1.2-1.4(1H,m), 1.5-1.65(1H,m), 1.7-2.0(3H,m), 2.15-2.3(6H,s), 2.6-2.75(4H,t), 2.75-2.9(1H,d), 2.95-3.1(1H,d), 4.0-4.3(4H,m), 5.5(1H,s), 6.9-7.05(3H,m), 7.1(2H,s) and 7.25-7.4(2H,m); m/z 392 (M+H).

Workup

  1. extractionextracting the aqueous mixture
  2. customobtained
  3. customthere was obtained

Sources & evidence

ORD record
ord-83ef86cc7d30428aac378f15bc1b7f80
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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