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

HRID 484616노트

반응식

HRID 484616 반응식
[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].[O:43]1CCC[CH2:44]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC.C(OCC)(=O)C>[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[CH2:44][OH:43])=[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]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 15030160Ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoateHCID 21226445Aluminium lithium hydride

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 42.36 ml of 1 molar lithium aluminum hydride in either is added dropwise under argon over 20 minutes a solution of ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoate in 50 ml of either 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.

후처리

  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

출처 및 근거

ORD 기록
ord-ee09bea64a054d299e44e9da5f60ae67
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05231182

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