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o-Toluenesulfonyl chloride → Trans-10a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6a,9,10,10a-tetrahydro-6H,7H-benzo[c]chromen-8-one

HRID 564324
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HRID 564324 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C@@:11]23[CH2:24][CH2:23][C:18]4(OCC[O:19]4)[CH2:17][C@H:16]2[CH2:15][O:14][C:13]2[C:25]([F:30])=[CH:26][CH:27]=[C:28]([F:29])[C:12]3=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(C)C(S(Cl)(=O)=O)=CC=CC=1>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C@@:11]23[CH2:24][CH2:23][C:18](=[O:19])[CH2:17][C@H:16]2[CH2:15][O:14][C:13]2[C:12]3=[C:28]([F:29])[CH:27]=[CH:26][C:25]=2[F:30])(=[O:10])=[O:9])=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 8623o-Toluenesulfonyl chlorideHCID 86614614Trans-10a-[(4-chlorophenyl)sulfonyl]-1,4-difluoro-6a, 9,10,10a-tetrahydrospiro[6H-dibenzo[b,d]pyran-8(7H), 2'-[1,3]dioxolane]

생성물 1

HCID 67006743Trans-10a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6a,9,10,10a-tetrahydro-6H,7H-benzo[c]chromen-8-one

시약·촉매·용매 2

HCID 180Acetone용매HCID 962
Water
용매

실험 절차

Trans-10a-[(4-chlorophenyl)sulfonyl]-1,4-difluoro-6a,9,10,10a-tetrahydrospiro[6H-dibenzo[b,d]pyran-8(7H), 2′-[1,3]dioxolane] (3.1 g, 6.8 mmole) was dissolved in 200 ml acetone and 10 ml water. Toluenesulfonyl chloride (1 g) was added and the mixture was refluxed overnight. Acetone was removed. 100 water and 100 ml EtOAc were added. The organic layer washed with water (50 ml), dried over Na2SO4 and concentrated. The residue was pure enough for next step. Yield: 2.8 g, 100%. 1H NMR (CDCl3 400 MHz δ 7.63 (d, J=8.1 Hz, 2H), 7.52 (d, J=8.8 Hz, 2H), 7.14 (m, 1H), 6.64 (m, 1H), 5.27 (dd, J=11.7 and 2.9 Hz, 1H), 4.13 (d, J=11.7 Hz, 1H), 3.18 (d, J=12.4 Hz, 1H), 2.79 (dt, J=12.4 and 3.7 Hz, 1H), 2.4-2.57 (m, 4H), 2.04-2.17 (m, 1H).

후처리

  1. temperaturethe mixture was refluxed overnight
  2. customAcetone was removed
  3. addition100 water and 100 ml EtOAc were added
  4. washThe organic layer washed with water (50 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-33aca515f90e4bb29c1fc64af6212b6f
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067621B2

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