Triethylamine → HCID 86669874, compound

HRID 1506322Notes

Reaction equation

HRID 1506322 reaction equation
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([C:10]2[O:14][N:13]=[C:12]3[C:15]4[C:20]([CH2:21][CH2:22][C:11]=23)=[CH:19][C:18]([CH:23]=C)=[CH:17][CH:16]=4)[C:6]=1[C:25]([F:28])([F:27])[F:26])[CH:2]([CH3:4])[CH3:3].[O:29]=[O+][O-].C(N(CC)CC)C>ClCCl>[CH2:1]([C:5]1[O:9][N:8]=[C:7]([C:10]2[O:14][N:13]=[C:12]3[C:15]4[C:20]([CH2:21][CH2:22][C:11]=23)=[CH:19][C:18]([CH:23]=[O:29])=[CH:17][CH:16]=4)[C:6]=1[C:25]([F:27])([F:26])[F:28])[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24823Ozone2×HCID 67170761HCID 67170761, compound

Product 1

HCID 86669874HCID 86669874, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-isobutyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 5D, 0.045 g, 0.116 mmol) in dichloromethane (10 mL) at −78° C. was passed ozone from an ozone generator until the solution turned deep blue. The reaction mixture then was purged with oxygen until the blue color disappeared and then with nitrogen for 5 min. The reaction mixture was allowed to warm to room temperature, and triethylamine (0.016 mL, 0.116 mmol) was added. The reaction mixture was stirred at room temperature for 15 min. and then concentrated under pressure to give 3-(5-isobutyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (0.045 g, 85% yield) as a tan solid. The product had an HPLC ret. time=4.02 min. (condition B); LC/MS M+1=391.09.

Workup

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

Sources & evidence

ORD record
ord-31486de3bb46408f804e1d15f5351103
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…