Ozone → HCID 67006379, compound

HRID 564349Notes

Reaction equation

HRID 564349 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:20][CH:9]2[CH2:10][O:11][C:12]3[C:17]([C:8]2([S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:7][CH2:6]1)=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[F:19])[CH:2]=C.[O:31]=[O+][O-].[BH4-].[Na+]>CO.C(Cl)Cl>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([S:21]([C:8]23[CH2:7][CH2:6][CH:5]([O:4][CH2:1][CH2:2][OH:31])[CH2:20][CH:9]2[CH2:10][O:11][C:12]2[C:17]3=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:23])=[O:22])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 67006734HCID 67006734, compound

Product 1

HCID 67006379HCID 67006379, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 8-allyloxy-10a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene (1.55 g, 3.41 mmol) in 1:1 MeOH/CH2Cl2 (30 mL) at −78° C. was purged with O3 until a blue color persisted. The reaction mixture was then purged with nitrogen until the blue color dissipated, NaBH4 (0.39 g, 10.2 mmol) was added and the reaction mixture was warmed slowly to ambient temperature, After 18 h, the reaction mixture was quenched with saturated aqueous NH4Cl and concentrated in vacuo. The residue was diluted with water and extracted with CH2Cl2 (3×). The combined organic extracts were washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo to afford the title compound (1.46 g, 93%): 1H NMR (CDCl3 400 MHz) δ 7.60 (d, J=8.8 Hz, 2H), 7.50 (d, J=8.8 Hz, 2H), 7.06 (m, 1H), 6.41 (m, 1H), 5.23 (dd, J=11.7, 3.7 Hz, 1H), 4.13 (d, J=11.7 Hz, 1H), 3.76 (t, J=5.1 Hz, 2H), 3.56-3.50 (m, 3H), 2.99 (m, 1H), 2.40-2.30 (m, 2H), 1.96-1.84 (m, 2H), 1.60 (br s, 1H), 1.54 (m, 1H), 1.16 (m, 1H).

Workup

  1. customThe reaction mixture was then purged with nitrogen until the blue color
  2. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with CH2Cl2 (3×)
  6. washThe combined organic extracts were washed with saturated aqueous NaHCO3
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5216ff1d7fec467f8db2879bbf4ca41a
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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