Ammonium Chloride → Methyl 4-[(4E)-5-(2-hydroxyphenyl)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}pent-4-en-1-yl]benzoate

HRID 1512202노트

반응식

HRID 1512202 반응식
C([Li])CCC.[Br-].[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:34]([CH:36]([CH2:49][CH2:50][C:51]1[CH:60]=[CH:59][C:54]([C:55]([O:57][CH3:58])=[O:56])=[CH:53][CH:52]=1)[CH2:37][CH2:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=1)=O.[Cl-].[NH4+]>CCCCCC.C1COCC1.O.C(OCC)(=O)C>[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1/[CH:10]=[CH:34]/[CH:36]([CH2:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:47][CH:48]=1)[CH2:49][CH2:50][C:51]1[CH:60]=[CH:59][C:54]([C:55]([O:57][CH3:58])=[O:56])=[CH:53][CH:52]=1

참가 물질

9

반응물 4

HCID 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 59397497Dimethyl 4,4'-(3-formylpentane-1,5-diyl)dibenzoateHCID 178418339Butyllithium

생성물 1

HCID 59397502Methyl 4-[(4E)-5-(2-hydroxyphenyl)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}pent-4-en-1-yl]benzoate

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

At 0° C., 2.95 ml (7.39 mmol) of a 2.5 M solution of n-butyllithium in hexane are slowly added dropwise to a solution of 1422 mg (3.2 mmol) of (2-hydroxybenzyl)(triphenyl)phosphonium bromide in 40 ml of THF. The reaction mixture is stirred at this temperature for 45 min. At 0° C., 1080 mg (2.64 mmol) of dimethyl 4,4′-(3-formylpentane-1,5-diyl)dibenzoate in 10 ml of THF are then metered in slowly. The reaction solution is stirred at 0° C. for 5 h, saturated ammonium chloride solution is then added and the mixture is diluted with water and ethyl acetate. The organic phase is separated off and the aqueous phase is extracted two more times with ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered, and the solvent is removed to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gives 169 mg (0.37 mmol, 14% of theory) of a colorless oil.

후처리

  1. customAt 0° C.
  2. stirringThe reaction solution is stirred at 0° C. for 5 h
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted two more times with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed to dryness

출처 및 근거

ORD 기록
ord-960ebd7b5cab4a56a1beccc63fbe304e
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217063B2

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