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Water → 5-(4-Fluorophenyl)-6-{fluoro[4-(trifluoromethoxy)phenyl]methyl}-7-isopropylspiro[chromen-2,1'-cyclobutan]-4(3H)-one

HRID 1516723
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HRID 1516723 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:20]([CH:21](O)[C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[C:19]([CH:34]([CH3:36])[CH3:35])[CH:18]=[C:17]3[C:9]=2[C:10](=[O:37])[CH2:11][C:12]2([O:16]3)[CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:44])CC)C.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:20]([CH:21]([F:44])[C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:26][CH:27]=3)=[C:19]([CH:34]([CH3:36])[CH3:35])[CH:18]=[C:17]3[C:9]=2[C:10](=[O:37])[CH2:11][C:12]2([O:16]3)[CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 580029385-(4-Fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropylspiro[chromen-2,1'-cyclobutan]-4(3H)-one

생성물 1

HCID 580029745-(4-Fluorophenyl)-6-{fluoro[4-(trifluoromethoxy)phenyl]methyl}-7-isopropylspiro[chromen-2,1'-cyclobutan]-4(3H)-one

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
-78 °C

실험 절차

Under argon, 159 mg (0.31 mmol) of 5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]-methyl}-7-isopropylspiro[chromen-2,1′-cyclobutan]-4(3H)-one (Example 58A) are dissolved in 3.1 ml of toluene, 49 μl (0.37 mmol) of diethylaminosulfur trifluoride are slowly added at −78° C. and the mixture is stirred at −78° C. for 2 h. Water is then added, and the mixture is extracted twice with ethyl acetate. The combined organic phases are washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution, and dried over sodium sulfate, filtered and concentrated. The crude product is purified on a silica gel column (mobile phase:cyclohexane/ethyl acetate 15:1). This gives 118 mg (74% of theory) of the title compound.

후처리

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. washThe combined organic phases are washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified on a silica gel column (mobile phase:cyclohexane/ethyl acetate 15:1)

출처 및 근거

ORD 기록
ord-bab78db1c2654baba31be4d9d988227f
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08227511B2

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