Ethyl bromoacetate → ethyl [6-cyano-1-(1-trityl-1H-imidazol-4-yl)-1,2,3,4-tetrahydronaphthalen-1-yloxy]acetate

HRID 1095447Notes

Reaction equation

HRID 1095447 reaction equation
[H-].[Na+].[OH:3][C:4]1([C:16]2[N:17]=[CH:18][N:19]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=2)[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([C:14]#[N:15])[CH:7]=[CH:6][C:5]1=2.Br[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43].C(=O)(O)[O-].[Na+]>O1CCCC1>[C:14]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([C:16]1[N:17]=[CH:18][N:19]([C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=1)([O:3][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:13][CH2:12][CH2:11]2)#[N:15]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 667819655-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 86632962ethyl [6-cyano-1-(1-trityl-1H-imidazol-4-yl)-1,2,3,4-tetrahydronaphthalen-1-yloxy]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.9 mmol of sodium hydride (60% dispersion in oil) are added in portions to a solution of 1.3 mmol of 5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile in 10 ml of tetrahydrofuran, and the mixture is stirred under reflux for 1 hour. 3.0 mmol of ethyl bromoacetate [105-36-2] are added and the reaction mixture is stirred under reflux for 8-16 hours. The reaction mixture is cooled and poured into saturated sodium bicarbonate solution and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of its Rf by flash chromatography (SiO2 60F).

Workup

  1. temperatureunder reflux for 1 hour
  2. stirringthe reaction mixture is stirred
  3. temperatureunder reflux for 8-16 hours
  4. temperatureThe reaction mixture is cooled
  5. extractionextracted with tert-butyl methyl ether (2×)
  6. washThe combined organic phases are washed with water and brine
  7. dry with materialdried with sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-abd81729f2854b6caee1f0b394217b26
Source dataset
uspto-grants-2012_03
Patent number
US08138179B2

Reaction notes

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