Tetrahydrofuran → HCID 25057141, compound

HRID 2422507Notes

Reaction equation

HRID 2422507 reaction equation
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH2:23]([C:25]([OH:30])([CH2:28][CH3:29])[C:26]#[CH:27])[CH3:24].C1COCC1>C(OCC)(=O)C.[Cu](I)I>[CH2:26]([C:25]([C:23]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=4)=[CH:10][C:11](=[O:15])[O:12]3)=[CH:7][CH:6]=2)[CH:24]=1)([OH:30])[CH2:28][CH3:29])[CH3:27]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 226983-Ethyl-1-pentyn-3-olHCID 86621971HCID 86621971, compound

Product 1

HCID 25057141HCID 25057141, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-(azidomethyl)-4-(3-methylphenyl)-2H-chromen-2-one (100 mg, 0.34 mmol) and 3-ethyl-1-pentyn-3-ol (46 mg, 0.41 mmol) in THF (4 mL) N,N-diisopropylethylamine (296 uL, 1.7 mmol) and copper iodide (97 mg, 0.51 mmol) were added. After overnight stirring, the reaction was diluted with ethyl acetate, filtered and washed with water and brine. The organic layer was then dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (acetone/CH2Cl2 20:80) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.90 (s, 1H), 7.54 (d, 1H), 7.47 (t, 1H), 7.43-7.33 (m, 4H), 7.25 (d, 1H), 6.33 (s, 1H), 5.78 (s, 2H), 3.70 (s, 1H), 2.45 (s, 3H), 1.95-1.75 (m, 4H), 0.79 (t, 6H).

Workup

  1. filtrationfiltered
  2. washwashed with water and brine
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. customwas purified by column chromatography (acetone/CH2Cl2 20:80)

Sources & evidence

ORD record
ord-0f24aded7bbb4e8b81f6057cd1dd68db
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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