Sulfuric Acid → 4'-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-cyanobi-phenyl

HRID 440206ノート

反応式

HRID 440206 の反応式
[CH2:1]([C@H:9]([C@H:12]([OH:14])[CH3:13])[CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)#[N:16].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CCCCCC.C(Cl)Cl.O.C1(C)C=CC=CC=1>[CH2:1]([C@H:9]1[CH2:10][O:11][C@H:29]([C:26]2[CH:25]=[CH:24][C:23]([C:20]3[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[CH:18][CH:19]=3)=[CH:28][CH:27]=2)[O:14][C@@H:12]1[CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

10

反応物 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 27592144'-Formyl-biphenyl-4-carbonitrileHCID 57227381(2S,3R)-2-octyl-1,3-butanediol

生成物 1

HCID 677427084'-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-cyanobi-phenyl収率 85.7%

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3.0 g of (2S,3R)-2-octyl-1,3-butanediol, 3.07 g of 4'-cyano-4-biphenylcarboxaldehyde, 0.1 ml of 1N sulfuric acid and 30 ml of toluene was placed under nitrogen in a round flask having a magnetic stirrer, water separator and condenser. The mixture was heated to reflux for 3 hours while separating water. The cooled reaction mixture was poured into aqueous sodium hydrogen carbonate solution and treated with methylene chloride. The aqueous phase was separated and extracted twice with methylene chloride. The combined organic phases were washed twice with water, dried over magnesium sulfate, filtered and evaporated. Recrystallization of the crude product obtained (5.84 g) from a mixture of 200 ml of hexane and 25 ml of ethyl acetate gave 4.97 g of 4'-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-cyanobi-phenyl with m.p. (C-SA) 114.5° C., cl.p. (SA -I) 128.4° C.

後処理

  1. customwas placed under nitrogen in a round flask
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 3 hours
  4. customwhile separating water
  5. customThe cooled reaction mixture
  6. customThe aqueous phase was separated
  7. extractionextracted twice with methylene chloride
  8. washThe combined organic phases were washed twice with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customRecrystallization of the crude product
  13. customobtained (5.84 g)

出典と根拠

ORDレコード
ord-843bcc92eced452aaf5e0be8b58223a6
出典データセット
uspto-grants-1996_05
特許番号
US05518653

反応ノート

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