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

HRID 1095447노트

반응식

HRID 1095447 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-abd81729f2854b6caee1f0b394217b26
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138179B2

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