Triethylamine → HCID 20229908, compound

HRID 2290691Notes

Reaction equation

HRID 2290691 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.C(N(CC)CC)C.[CH2:14]([S:16][C:17]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:28]=2[Cl:34])=[CH:22][C:18]=1[C:19](Cl)=[O:20])[CH3:15]>C1(C)C=CC=CC=1>[CH2:14]([S:16][C:17]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:28]=2[Cl:34])=[CH:22][C:18]=1[C:19]([O:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1)=[O:20])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99603-Furanol, tetrahydro-HCID 20229912HCID 20229912, compound

Product 1

HCID 20229908HCID 20229908, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-Hydroxytetrahydrofuran (0.04 mole), toluene (50 ml) and triethylamine (0.04 mole) are charged into a glass reaction vessel equipped with a mechanical stirrer and addition funnel. A solution of 2-ethylthio-5-(2-chloro-4-bromophenoxy)benzoyl chloride (0.04 mole) in toluene (20 ml) is slowly added at room temperature with stirring. After the addition is completed, stirring is continued for a period of about eight hours. After this time, the reaction mixture is washed with water and dried over anhydrous magnesium sulfate. The dried solution is then stripped of solvent under reduced pressure leaving a residue. This residue is purified by silica gel chromatography using toluene and ethyl acetate/toluene mixture as the eluant to yield the desired product 3-tetrahydrofuryl 2-ethylthio-5-(2-chloro-4-bromophenoxy)benzoate.

Workup

  1. customequipped with a mechanical stirrer and addition funnel
  2. additionAfter the addition
  3. stirringstirring
  4. washAfter this time, the reaction mixture is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customleaving a residue
  7. customThis residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-275582f292844232a8901c56107dbdc7
Source dataset
uspto-grants-1986_10
Patent number
US04618359

Reaction notes

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