Triethylamine → HCID 86669917, compound

HRID 1506464Notes

Reaction equation

HRID 1506464 reaction equation
[CH:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]=C)=[CH:19][CH:18]=5)[C:8]=2[C:27]([F:30])([F:29])[F:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:31]=[O+][O-].C(N(CC)CC)C>ClCCl>[CH:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]=[O:31])=[CH:19][CH:18]=5)[C:8]=2[C:27]([F:30])([F:29])[F:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24823Ozone2×HCID 67171805HCID 67171805, compound

Product 1

HCID 86669917HCID 86669917, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-cyclohexyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 75A, 0.015 g, 0.036 mmol) in dichloromethane (5.0 mL) at −78° C. was passed ozone from an ozone generator until the solution turned a deep blue. The reaction mixture was then purged with oxygen until the blue color disappeared and then with nitrogen for 5 minutes. The reaction mixture was allowed to warm to room temperature, and triethylamine (5.07 μl, 0.036 mmol) was added. The reaction mixture was stirred at room temperature for 15 minutes. Concentration under vacuum provided 3-(5-cyclohexyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde [0.014 g, 0.0.036 mmol, 98%] as a tan solid. The product had an HPLC ret. time=4.44 min. (condition B). LC/MS M+1=417.07.

Workup

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

Sources & evidence

ORD record
ord-b7160b7f719b4119b2a4736778b95aa0
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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