p-Toluenesulfonic acid → HCID 19801181, compound

HRID 1646603Notes

Reaction equation

HRID 1646603 reaction equation
C[Si](C)(C)[O:3][C:4]1[C:12]2[C:7](=[C:8]([CH2:13][CH:14]=[CH2:15])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]=1.[Cl:18]N1C(=O)CCC1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.P(O)(O)([O-])=O.[K+]>ClCCCl.ClC(Cl)C>[Cl:18][CH:5]1[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][CH:14]=[CH2:15])[C:4]1=[O:3]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 31398Chlorosuccinimide2×HCID 516951Monobasic potassium phosphateHCID 19801182HCID 19801182, compound

Product 1

HCID 19801181HCID 19801181, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

8 g of 3-trimethylsilyloxy-7-(2-propenyl)-indene in 25 ml of 1,2-dichloroethane is cooled to 0° C.; 31 g of N-chlorosuccinimide in 80 ml of dichloroethane is introduced over 25 minutes, with agitation for 30 minutes at 0° C.; 0.6 g of N-chlorosuccinimide in 15 ml of dichloroethane and a few mg of paratoluene sulphonic acid are added. After 30 minutes of agitation at 0° C., the reaction mixture is poured over an iced aqueous solution saturated with monopotassium phosphate, with agitation for 16 hours at 20° C. After decanting and extracting with methylene chloride, the extracts are dried, and concentrated to dryness under reduced pressure. The residue is chromatographed on silica, eluting with a hexane-isopropyl ether mixture (7-3). The fractions recovered are concentrated and chromatographed again on silica, eluting with a hexane-isopropyl ether mixture (3-1) and 2.75 g of expected product is isolated.

Workup

  1. customAfter decanting
  2. extractionextracting with methylene chloride
  3. customthe extracts are dried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue is chromatographed on silica
  6. washeluting with a hexane-isopropyl ether mixture (7-3)
  7. customThe fractions recovered
  8. concentrationare concentrated
  9. customchromatographed again on silica
  10. washeluting with a hexane-isopropyl ether mixture (3-1)

Sources & evidence

ORD record
ord-1c17a3994839450d86561c344de848fa
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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