Butyryl chloride → (+)-2-(4-(3-Butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine

HRID 1735985

반응식

HRID 1735985 반응식
[OH:1][CH:2]([CH3:28])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:7][CH:6]=1.[C:29](Cl)(=[O:33])[CH2:30][CH2:31][CH3:32]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:29]([O:1][CH:2]([CH3:28])[CH:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:9][CH:10]=1)(=[O:33])[CH2:30][CH2:31][CH3:32]

참가 물질

5

반응물 2

HCID 8855Butyryl chlorideHCID 54343164(-)-2-(4-(3-Hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine

생성물 1

HCID 54572593(+)-2-(4-(3-Butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine수율 88.7%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 1140Toluene용매

실험 절차

1.0 g of (-)-2-(4-(3-hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine, added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order. The toluene layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.05 g of (+)-2-(4-(3-butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine.

후처리

  1. washwashed with 4N hydrochloric acid, water
  2. concentrationThe toluene layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-fbc540d83834464ea79de90baacc446a
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05539115

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