Tetrahydrofuran → HCID 22757269, compound

HRID 65626Notes

Reaction equation

HRID 65626 reaction equation
[CH2:1]([C:3]1([CH2:16][C:17]([OH:19])=[O:18])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][CH2:5][CH2:4]1)[CH3:2].[H-].[Na+].O1CCC[CH2:23]1>>[CH2:1]([C:3]1([CH2:16][C:17]([OH:19])=[O:18])[C:15]2[N:14]([CH3:23])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 122920371-Ethyl 1,2,3,4-tetrahydrocarbazole-1-acetic acid

Product 1

HCID 22757269HCID 22757269, compound

Conditions

Temperature
40 °C

Procedure

A solution of the compound of formula 5, 1-ethyl 1,2,3,4-tetrahydrocarbazole-1-acetic acid (2.0 g, 7.4 mmole), described in Example 56, in dry tetrahydrofuran (THF, 50 ml) is added dropwise under nitrogen to a stirred suspension of sodium hydride (1 g, 50% dispersion, 0.02 mole) in dry-THF (25 ml). The reaction mixture is stirred for 15 minutes after the end of the addition. The lower alkyl halide, methyliodide (1.5 ml), is added dropwise. The reaction mixture is heated initially to 40° C. then stirred for one hour at room temperature. A small amount of water is added cautiously to destroy excess sodium hydride followed by the addition of more water (50 ml). The mixture is washed with ether then rendered acidic and extracted with ether. The ether extract is dried (MgSO4), treated with charcoal and filtered through diatomaceous earth. Evaporation of the ether gives an oil which on recrystallization from benzene affords the title compound, mp 140°-143° C., nmr (CDCl3) δ 0.72 (t, J = 7, 3H), 1.9 (m, 6H), 2.75 (m, 4H), 3.76 (s, 3H), 7.2 (m, 4H).

Workup

  1. dry with materialin dry-THF (25 ml)
  2. additionafter the end of the addition
  3. additionThe lower alkyl halide, methyliodide (1.5 ml), is added dropwise
  4. stirringthen stirred for one hour at room temperature
  5. additionA small amount of water is added cautiously
  6. customto destroy excess sodium hydride
  7. additionfollowed by the addition of more water (50 ml)
  8. washThe mixture is washed with ether
  9. extractionextracted with ether
  10. extractionThe ether extract
  11. dry with materialis dried (MgSO4)
  12. additiontreated with charcoal
  13. filtrationfiltered through diatomaceous earth
  14. customEvaporation of the ether
  15. customgives an oil which
  16. customon recrystallization from benzene

Sources & evidence

ORD record
ord-00a1f2c9e718443eb5e914071d5314cb
Source dataset
uspto-grants-1978_12
Patent number
US04128560

Reaction notes

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