Ethyl Acetate → [2-[4-(Tetradecyloxy)phenyl]ethyl]aminobenzenemethanol

HRID 653792ノート

反応式

HRID 653792 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=2)C(OCC)=O)=O)=[CH:24][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:43](OCC)(=[O:45])C.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC.O1CCCC1>[CH2:7]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][NH:31][C:32]2[CH:42]=[CH:41][CH:40]=[CH:34][C:33]=2[CH2:43][OH:45])=[CH:26][CH:27]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 15030160Ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 86745967[2-[4-(Tetradecyloxy)phenyl]ethyl]aminobenzenemethanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 42.36 ml of 1 molar lithium aluminum hydride in ether is added dropwise under argon over 20 minutes a solution of ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoate in 50 ml of ether and 50 ml of tetrahydrofuran. The mixture is refluxed for 3 hours, cooled to 0° C. and ethyl acetate added. Saturated sodium sulfate is added followed by ether. The mixture is filtered and the cake washed with ether. The filtrate is evaporated and the residue chromatographed on silica gel using 9:1 chloroform:ethyl acetate. The product fractions are combined and evaporated to a residue which is crystallized from hexane to give 4.5 g of the desired product as a white solid, m.p. 67°-70° C.

後処理

  1. temperatureThe mixture is refluxed for 3 hours
  2. filtrationThe mixture is filtered
  3. washthe cake washed with ether
  4. customThe filtrate is evaporated
  5. customthe residue chromatographed on silica gel using 9:1 chloroform
  6. customevaporated to a residue which
  7. customis crystallized from hexane

出典と根拠

ORDレコード
ord-a307d95270954175b42259dc9a7ed31b
出典データセット
uspto-grants-1992_07
特許番号
US05128351

反応ノート

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