Triethylamine → HCID 86669913, compound

HRID 1506453Notes

Reaction equation

HRID 1506453 reaction equation
[CH3:1][C:2]1[CH:29]=[C:28]2[C:5]([CH2:6][CH2:7][C:8]3[C:9]2=[N:10][O:11][C:12]=3[C:13]2[C:17]([C:18]([F:21])([F:20])[F:19])=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:15][N:14]=2)=[CH:4][C:3]=1[CH:30]=C.[O:32]=[O+][O-].C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[CH:29]=[C:28]2[C:5]([CH2:6][CH2:7][C:8]3[C:9]2=[N:10][O:11][C:12]=3[C:13]2[C:17]([C:18]([F:21])([F:19])[F:20])=[C:16]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:15][N:14]=2)=[CH:4][C:3]=1[CH:30]=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24823Ozone2×HCID 67170771HCID 67170771, compound

Product 1

HCID 86669913HCID 86669913, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 64E, 0.058 g, 0.137 mmol) in dichloromethane (10 mL) at −78° C. was passed ozone from an ozone generator until the solution turned a deep blue. The reaction mixture then was purged with oxygen until the blue color disappeared, then with nitrogen for five minutes. The reaction mixture was allowed to warm to room temperature and triethylamine (0.019 mL, 0.137 mmol) was added. The reaction mixture was stirred at room temperature for fifteen minutes and then concentrated under vacuum to give 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde as a tan solid (0.043, 0.101 mmol, 74%). The product had an HPLC ret. time=3.43 min (condition B). LC/MS M+1=425.10.

Workup

  1. customat −78° C.
  2. customThe reaction mixture then was purged with oxygen until the blue color
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1d2f02e035784a6da128a21da2a07949
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…