Ethanol → 1-Cyano-4-[beta-(1H-imidazol-1-yl)ethoxy]indane

HRID 64901Notes

Reaction equation

HRID 64901 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][C:13]3=O)[CH:5]=[CH:4][N:3]=[CH:2]1.C1(C)C=CC(S([CH2:28][N+:29]#[C-])(=O)=O)=CC=1.[Na].C(O)C>C(COC)OC>[C:28]([CH:13]1[C:14]2[C:10](=[C:9]([O:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]1)#[N:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 161915Tosylmethyl isocyanideHCID 5360545SodiumHCID 202358824-[beta-(1H-imidazol-1-yl)ethoxy]-1-indanone

Product 1

HCID 202358761-Cyano-4-[beta-(1H-imidazol-1-yl)ethoxy]indaneYield 32%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 2.68 g 4-[β-(1H-imidazol-1-yl)ethoxy]-1-indanone and 3.3 g of (p-toluenesulfonyl)methylisocyanide in 80 ml of dimethoxyethane, 0.36 g of sodium dissolved in 13.5 of absolute ethanol and 29 ml of dimethoxyethane are added as described in Ex. 3. 2.9 g of crude product are isolated and under purification by silica-gel chromatography allows to isolate 0.86 g (32%) of the nitrile in the form of oil which solidifies along the time (M.P. 115°-117° C.) and is chromatographically pure.

Workup

  1. additionare added
  2. custom2.9 g of crude product are isolated and under purification by silica-gel chromatography

Sources & evidence

ORD record
ord-8fdff02f7558433fa2eea957e6518395
Source dataset
uspto-grants-1986_09
Patent number
US04610998

Reaction notes

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