Triethylamine → HCID 19025174, compound

HRID 1033144Notes

Reaction equation

HRID 1033144 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH:3]=1.C(N(CC)CC)C.[C:20](Cl)(=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].CN(C1C=CC=CN=1)C>ClCCl.CCCCCC.C(OCC)(=O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][C:20](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 69819Nonanoyl chlorideHCID 935522,6-Dihydroxynaphthalene

Product 1

HCID 19025174HCID 19025174, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

2,6-dihydroxynaphthalene (0.48 g) and triethylamine (0.31 g) were dissolved in 20 ml of dichloromethane. Nonanoyl chloride (0.55 g) and dimethylaminopyridine (0.13 g) were added to the solution, and the mixture was stirred at room temperature for about 20 hours. The reaction mixture was poured into ice-water, extracted with dichloromethane and dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation to give a crude product, which was treated with a silica gel column chromatograph (eluent: hexane/ethyl acetate=10/2) to give 0.29 g of the desired product.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed by evaporation
  4. customto give a crude product, which

Sources & evidence

ORD record
ord-088814e356214246ad141220c6ab0563
Source dataset
uspto-grants-1994_05
Patent number
US05310500

Reaction notes

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