Propargyl bromide → 1,2,3,4-tetrahydro-9-(2-propynyl)-9H-carbazole

HRID 1032783Notes

Reaction equation

HRID 1032783 reaction equation
[K].[CH2:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:15](Br)[C:16]#[CH:17]>CN(C)C=O.O>[CH2:17]([N:13]1[C:14]2[CH2:2][CH2:3][CH2:4][CH2:5][C:6]=2[C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:16]#[CH:15]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 136641,2,3,4-TetrahydrocarbazoleHCID 5462222Potassium

Product 1

HCID 127119101,2,3,4-tetrahydro-9-(2-propynyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium tert.-buroxide, 3.6 g (33 mmol), was added to a solution of 5 g (30 mmol) of 1,2,3,4-tetrahydro-9H-carbazole in 50 ml of dimethylformamide. After stirring for 45 minutes under nitrogen, 3.9 g or 2.9 ml (33 mmol) of propargyl bromide was added and stirring was continued for 30 minutes at room temperature followed by 45 minutes on the steam bath. The cooled reaction mixture was diluted with water and the product was extracted with ether. The extracts were washed with water, dried over sodium sulfate and evaporated. The residue was passed over a plug of silica gel using methylene chloride/hexane 1:1. The fractions containing the least polar product were combined and evaporated. The residue was crystallized from hexane to give colorless crystals of 1,2,3,4-tetrahydro-9-(2-propynyl)-9H-carbazole with m.p. 74°-76°.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes at room temperature
  3. waitfollowed by 45 minutes on the steam bath
  4. customThe cooled reaction mixture
  5. extractionthe product was extracted with ether
  6. washThe extracts were washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. additionThe fractions containing the least polar product
  10. customevaporated
  11. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-d62b8789b84146ea95b7e07af1af7f3d
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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