Ozone → HCID 86624769, compound

HRID 1643832Notes

Reaction equation

HRID 1643832 reaction equation
[CH3:1][S:2]([C:5]1[CH:28]=[CH:27][C:8]([O:9][C:10]2[C:11]([CH:24]=CC)=[C:12]([C:20]([O:22][CH3:23])=[O:21])[CH:13]=[C:14]([CH:19]=2)[C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[O:29]=[O+][O-]>C(Cl)Cl.CO>[CH:24]([C:11]1[C:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:28][CH:27]=2)=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[C:20]([O:22][CH3:23])=[O:21])=[O:29]

Participants

5

Reactant 2

HCID 24823OzoneHCID 66756428Dimethyl 5-(4-(methylsulfonyl)phenoxy)-4-(prop-1-enyl)isophthalate

Product 1

HCID 86624769HCID 86624769, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl 5-(4-(methylsulfonyl)phenoxy)-4-(prop-1-enyl)isophthalate (2.6 g, 7.8 mmol) in CH2Cl2 and methanol was cooled to −78° C. and treated with ozone until the solution appeared blue (20 min). Nitrogen was bubbled through the solution until the blue color dissipated. Dimethylsulfide (1.0 mL) was added and the cold-bath was removed allowing the reaction mixture to warm to room temperature overnight. Concentration of the solution under vacuum provided an oil, which was introduced into a silica gel column and eluted with 10-30% EtOAc in hexanes to afford the title compound (2.5 g, 98%) as a white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.08 (q, 3 H) 3.95 (dd, 6 H) 7.08-7.16 (m, 2 H) 7.98 (q, J=2.07 Hz, 2 H) 7.99-8.03 (m, 1 H) 8.33-8.39 (m, 1 H) 10.46 (s, 1 H); LC-MS (ERS)+ m/z=393.00 (M+H)+.

Workup

  1. custom(20 min)
  2. customNitrogen was bubbled through the solution until the blue color
  3. additionDimethylsulfide (1.0 mL) was added
  4. customthe cold-bath was removed
  5. customConcentration of the solution under vacuum provided an oil, which
  6. additionwas introduced into a silica gel column
  7. washeluted with 10-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-353f8302a44c46e7be295c0f2d649ce7
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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