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

HRID 1095446ノート

反応式

HRID 1095446 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-acebce3118a2471b93179e486f86a6d3
出典データセット
uspto-grants-2012_03
特許番号
US08138179B2

反応ノート

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