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

HRID 564324Notes

Reaction equation

HRID 564324 reaction equation
[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

Participants

5

Reactant 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]

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-33aca515f90e4bb29c1fc64af6212b6f
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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