Ammonium Chloride → Methyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate

HRID 1920585노트

반응식

HRID 1920585 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.[CH2:34]([O:36][C:37](=[O:58])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44]([CH:56]=O)[CH2:45][C:46]2[CH:55]=[CH:54][C:49]([C:50]([O:52][CH3:53])=[O:51])=[CH:48][CH:47]=2)[CH2:41][CH2:40]1)[CH3:35].[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:34]([O:36][C:37](=[O:58])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44](/[CH:56]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:45][C:46]2[CH:55]=[CH:54][C:49]([C:50]([O:52][CH3:53])=[O:51])=[CH:48][CH:47]=2)[CH2:41][CH2:40]1)[CH3:35]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57965769Methyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-formylbutyl}benzoateHCID 178418339Butyllithium

생성물 1

HCID 57965750Methyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

At 0° C., 4.11 ml (10.26 mmol) of a 2.5 M solution of n-butyllithium in hexane are added slowly to a solution of 2.471 g (5.5 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 25 ml of anhydrous THF, and the mixture is stirred for 45 min. At this temperature, 1.27 g (3.67 mmol) of methyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-formylbutyl}benzoate are then metered in slowly, and the mixture is stirred at 0° C. for two hours. After complete conversion, saturated ammonium chloride solution is added, and the reaction solution is concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is evaporated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gives 757 mg (47% of theory) of a yellowish oil.

후처리

  1. stirringis stirred at 0° C. for two hours
  2. concentrationthe reaction solution is concentrated to dryness
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is evaporated to dryness

출처 및 근거

ORD 기록
ord-1cd79492c4a44aabbaec829a50759187
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168821B2

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