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p-Toluenesulfonic acid → HCID 117940099, 화합물

HRID 2199838
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HRID 2199838 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:5][C:4]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CC1C=CC(S(O)(=O)=O)=CC=1.[F:37][C:38]([F:46])([F:45])[C:39]([C:41]([F:44])([F:43])[F:42])=[O:40]>C1(C)C=CC=CC=1.O>[F:37][C:38]([F:46])([F:45])[C:39]([C:18]1[CH:19]=[C:14]([CH2:13][CH:8]2[CH2:7][C:6]3[C:10](=[CH:11][C:3]([O:2][CH3:1])=[C:4]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:5]=3)[C:9]2=[O:12])[CH:15]=[N:16][CH:17]=1)([OH:40])[C:41]([F:44])([F:43])[F:42]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 12695HexafluoroacetoneHCID 117940187HCID 117940187, 화합물

생성물 1

HCID 117940099HCID 117940099, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
120 °C

실험 절차

To a stirred solution of 243 (0.08 g, 0.236 mmol) in toluene was added PTSA (0.090 g, 0.472 mmol) and kept stirring at 120° C. Hexafluoroacetone 244 (0.129 g, 0.590 mmol) was added to the reaction and heated to 100° C. for 16 h. Reaction was cooled to RT, diluted with water, extracted with ethyl acetate twice, the organic layer dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel eluting the compound at 30% ethyl acetate in hexane as thick sticky solid 2-((5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-3-yl)methyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 245. 1HNMR (400 MHz, CDCl3) δ ppm 7.06 (m, 2H), 6.88 (s, 1H), 6.90 (s, 1H), 6.123 (s, 1H), 3.88 (m, 7H), 3.49 (m, 1H), 3.08 (m, 2H), 3.03 (m, 6H), 2.29 (m, 2H).

후처리

  1. temperatureheated to 100° C. for 16 h
  2. customReaction
  3. temperaturewas cooled to RT
  4. extractionextracted with ethyl acetate twice
  5. dry with materialthe organic layer dried over sodium sulphate
  6. concentrationconcentrated
  7. customto get the crude, which
  8. customwas purified through flash chromatography

출처 및 근거

ORD 기록
ord-40c447eb4e4a4bc682dd3cdd00f4d5e8
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359315B2

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