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Water → 6-[(4-tert-Butylphenyl)(fluoro)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

HRID 1516720
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HRID 1516720 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[C:12]2[C:13]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[C:14]3[C:22](=[CH:23][C:24]=2[CH:25]([CH3:27])[CH3:26])[O:21][C:17]2([CH2:20][CH2:19][CH2:18]2)[CH2:16][C:15]3=[O:28])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:43])CC)C.O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([F:43])[C:12]2[C:13]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[C:14]3[C:22](=[CH:23][C:24]=2[CH:25]([CH3:26])[CH3:27])[O:21][C:17]2([CH2:18][CH2:19][CH2:20]2)[CH2:16][C:15]3=[O:28])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]
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참가 물질

5

반응물 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 580029576-[(4-tert-Butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

생성물 1

HCID 580030226-[(4-tert-Butylphenyl)(fluoro)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

시약·촉매·용매 1

HCID 1140
Toluene
용매

반응 조건

온도
-78 °C

실험 절차

Under argon, 110 mg (0.23 mmol) of 6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1′-cyclobutan]-4(3H)-one (Example 55A) are dissolved in 2.3 ml of toluene, 36 μl (0.27 mmol) of diethylaminosulfur trifluoride are added slowly at −78° C. and the mixture is stirred at −78° C. for 1 h. The temperature is then slowly increased to −60° C. After 2 h, water is 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, dried over sodium sulfate, filtered and concentrated. The crude product is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 12:1). This gives 92 mg (83% of theory) of the title compound.

후처리

  1. temperatureThe temperature is then slowly increased to −60° C
  2. waitAfter 2 h
  3. extractionthe mixture is extracted twice with ethyl acetate
  4. washThe combined organic phases are washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 12:1)

출처 및 근거

ORD 기록
ord-2407f9c0df3c4b1ba65fbbf53f06c7aa
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08227511B2

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