Water → HCID 68670895, compound

HRID 2192896Notes

Reaction equation

HRID 2192896 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[CH:18][C@@H:19]2[CH2:39][CH2:38][C:21]3([O:25][C@@H:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@H:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:22]3)[CH2:20]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8][CH:9]1[CH2:11][CH2:10]1.C(=O)([O-])[OH:41].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[OH2:56]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[CH:18][C@@H:19]2[CH2:39][CH2:38][C:21]3([O:22][C@@H:23]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@H:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:25]3)[CH2:20]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH:9]1[CH2:11][CH2:10]1)(=[O:41])=[O:56]

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 68671359HCID 68671359, compound

Product 1

HCID 68670895HCID 68670895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 2-[3-bromo-4-(cyclopropylsulfanyl)phenyl]-3-[(2S,3S,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]acrylate (2.58 g, (E)/(Z)-mixture) was dissolved in dichloromethane (77 mL), followed by ice-cooling. To this solution was added sodium hydrogen carbonate (7.87 g) and then m-chloroperbenzoic acid (2.31 g). It was stirred for 30 minutes under ice-cooling, and further warmed to room temperature, followed by stirring for 3 hours. Dichloromethane (55 mL) and m-chloroperbenzoic acid (0.32 g) were further added thereto, followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture to stop the reaction and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-[(2S,3S,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]acrylate (2.52 g) as an (E)/(Z)-mixture of olefin.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring for 3 hours
  4. stirringby stirring at room temperature for 1 hour
  5. customthe reaction
  6. customthe organic layer was separated
  7. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d0196e087dc4a89886784ade487009e
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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