Ozone → HCID 178521453, compound

HRID 271331Notes

Reaction equation

HRID 271331 reaction equation
CC(C)CC=[C:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:6][O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH2:10][CH2:9]1.[O:32]=[O+][O-]>ClCCl>[O:32]=[C:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:6][O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 178444127HCID 178444127, compound

Product 1

HCID 178521453HCID 178521453, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2 g of trans-2-[4-(5-methyl-2-phenyl-hex-2-enyloxy)-cyclohexyl]-isoindole-1,3-dione in 100 mL of dichloromethane cooled to −78° C. was dispersed a stream of ozone from an ozone generator until a blue color persisted. The excess ozone was purged with nitrogen until the blue color dissipated, and 5 mL of methyl sulfide was added. After warming to room temperature over 30 min, the solution was concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 2%-30% ethyl acetate in hexane gave 1.8 g of product as a white crystalline solid: 1H NMR (400 MHz, CDCl3) 8.0 (d, 2H), 7.8 (m, 2H), 7.6 (t, 1H), 7.5 (t, 2H), 4.8 (s, 2H), 4.18 (m, 1H), 3.5 (m, 1H), 2.35 and 2.25 (overlapping dd and d, 4H), 1.8 (d, 2H), 1.5 (dd, 2H).

Workup

  1. customThe excess ozone was purged with nitrogen until the blue color
  2. addition5 mL of methyl sulfide was added
  3. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-56cf2a7efeac40fba0efe73dd8df2097
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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