Triethylamine → HCID 13373093, compound

HRID 2290684Notes

Reaction equation

HRID 2290684 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.C(N(CC)CC)C.[N+:14]([C:17]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=2[Cl:37])=[CH:22][C:18]=1[C:19](Cl)=[O:20])([O-:16])=[O:15]>C1(C)C=CC=CC=1>[N+:14]([C:17]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][C:28]=2[Cl:37])=[CH:22][C:18]=1[C:19]([O:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1)=[O:20])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99603-Furanol, tetrahydro-HCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 13373093HCID 13373093, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-Hydroxytetrahydrofuran (1.76 grams; 0.02 mole), toluene (50 ml) and triethylamine (2.0 grams; 0.02 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer and addition funnel. A solution of 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride (7.60 grams; 0.02 mole) in toluene (10 ml) was slowly added with stirring. After the addition was completed, stirring was continued overnight. After this time, the reaction mixture was washed with water and dried over anhydrous sodium sulfate. The dried solution was then stripped of solvent under reduced pressure leaving a brown oil. This oil was purified by silica gel chromatography using toluene and ethyl acetate/toluene mixtures as the eluant. The purified oil was triturated in ethanol to yield the desired product 3-tetrahydrofuryl 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate as a white solid, melting point at 55° C.

Workup

  1. customequipped with a mechanical stirrer and addition funnel
  2. additionAfter the addition
  3. stirringstirring
  4. washAfter this time, the reaction mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customleaving a brown oil
  7. customThis oil was purified by silica gel chromatography
  8. customThe purified oil was triturated in ethanol

Sources & evidence

ORD record
ord-d11e03471a594d389670f97f32828128
Source dataset
uspto-grants-1986_10
Patent number
US04618359

Reaction notes

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