Hexane → 2-Ethyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

HRID 1357254Notes

Reaction equation

HRID 1357254 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]=1[C:8](Cl)=[O:9])[CH3:2].[CH3:15][NH:16][CH2:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([OH:28])[CH:22]=[CH:21]2.C(N(CC)CC)C.CCCCCC>C1COCC1.C(OCC)(=O)C>[OH:28][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH2:17][N:16]([CH3:15])[C:8]([C:7]1[C:6]3[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=3[O:4][C:3]=1[CH2:1][CH3:2])=[O:9])[CH:27]=[CH:26]2

Participants

7

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 185052756-Methylaminomethyl-naphthalen-2-olHCID 185052952-Ethyl-benzofuran-3-carbonyl chloride

Product 1

HCID 865873852-Ethyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amideYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Ethyl-benzofuran-3-carbonyl chloride, prepared in step 2 of Example 21, in 50 mL of anhydrous THF was added under nitrogen dropwise over 1 h to a suspension of 6-methylaminomethyl-naphthalen-2-ol (1.48 g, 7.9 mmol), prepared in the previous step, and triethylamine (1.1 mL, 7.9 mmol) in 150 mL anhydrous THF at room temperature. The reaction stirred at room temperature for 20 h (overnight). The solid present was removed by filtration and the filtrate concentrated under reduced pressure to give a brown foam. The foam was dissolved in ethyl acetate and extracted with 1N HCl. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a brown oil which solidified when treated with hexane. The crystals were triturated with hexane and dried under reduced pressure to give 2-ethyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (2.38 g, 84%) as tan solid, mp 80-90° C.

Workup

  1. customThe solid present was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give a brown foam
  4. extractionextracted with 1N HCl
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customto give a brown oil which
  8. customThe crystals were triturated with hexane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-c7380864eb8342e0b0cf6addc6aba1a7
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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