Sodium borohydride → 5-(2-hydroxyethoxy)-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1095446노트

반응식

HRID 1095446 반응식
[BH4-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:22]1[N:23]=[CH:24][N:25]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([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)[CH:26]=1)([O:15][CH2:16][C:17](OCC)=[O:18])[CH2:10][CH2:9][CH2:8]2)#[N:4]>C(O)C>[OH:18][CH2:17][CH2:16][O:15][C:11]1([C:22]2[N:23]=[CH:24][N:25]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([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)[CH:26]=2)[CH2:10][CH2:9][CH2:8][C:7]2[CH:6]=[C:5]([C:3]#[N:4])[CH:14]=[CH:13][C:12]1=2

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86632962ethyl [6-cyano-1-(1-trityl-1H-imidazol-4-yl)-1,2,3,4-tetrahydronaphthalen-1-yloxy]acetate

생성물 1

HCID 667821935-(2-hydroxyethoxy)-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
20 °C

실험 절차

3.0 mmol of sodium borohydride are added in portions to a solution of 1.0 mmol of ethyl [6-cyano-1-(1-trityl-1H-imidazol-4-yl)-1,2,3,4-tetrahydronaphthalen-1-yloxy]acetate in 5 ml of ethanol at 20° C. The reaction mixture is stirred at 20° C. for 2-6 hours and then evaporated. The residue is taken up in saturated aqueous sodium bicarbonate solution and dichloromethane, and the mixture is vigorously stirred for 10 minutes. The phases are separated and the aqueous phase is back-extracted with dichloromethane. The combined organic phases are 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. customevaporated
  2. stirringdichloromethane, and the mixture is vigorously stirred for 10 minutes
  3. customThe phases are separated
  4. extractionthe aqueous phase is back-extracted with dichloromethane
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. customevaporated

출처 및 근거

ORD 기록
ord-acebce3118a2471b93179e486f86a6d3
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138179B2

반응 노트

불러오는 중…