Tetrahydrofuran → HCID 22403953, compound

HRID 259825Notes

Reaction equation

HRID 259825 reaction equation
[CH:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=O.[H-].[Na+].[I-].CC(C)=C[SH2+].[N-:20]=[N+:21]=[N-:22].[Na+].C1C[O:27][CH2:26][CH2:25]1>CC(C)=O.O>[N:20]([CH:1]1[C:3]2=[CH:11][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]2[CH2:25][CH:26]1[OH:27])=[N+:21]=[N-:22]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 33557Sodium AzideHCID 96389Indole-2-carboxaldehydeHCID 86749533HCID 86749533, compound

Product 1

HCID 22403953HCID 22403953, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

In a 100-mL round-bottom flask, a total of 1.9 g (13 mmol) of 2-formylindole and 780 mg (26 mmol) of NaH (80% dispersion in mineral oil) was stirred in 150 mL of dry THF under N2 at 0° C. (ice bath). At total of 3.39 g (15.7 mmol) of dimethylvinylsulfonium iodide was added after 20 minutes, and then the reaction mixture was stirred overnight (about 15 hours). A total of 3.38 g of NaN3 (50 mmol) in 20 mL of 1:1 acetone:water was added to the reaction mixture, and then the reaction mixture was stirred at room temperature for about 12 hours. The mixture was evaporated under reduced pressure, and then purified by flash chromatography (3:2 petroleum ether:ethyl acetate). A yellow oil (2.0 g) was obtained (72%). 1H NMR (CDCl3): δ2.42 (d, 1H, J=5.5), 3.96 (dd, 1H, J=2.5, J2 =11), 4.39 (dd, 1H, J1 =5.5, J2 =11), 4.76 (m, 1H), 4.84 (br s, 1H), 6.56 (s, 1H), 7.10-7.39 (m, 3H), 7.65 (d, 1H, J=7.5). 13C NMR (CDCl3 (CDCl3): δ50.2, 64.6, 79.8, 96.4, 109.7, 119.8, 121.5, 122.1, 131.9, 132.9, 137.1.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for about 12 hours
  2. customThe mixture was evaporated under reduced pressure
  3. custompurified by flash chromatography (3:2 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-d204f9dcf0554ca5aa59239de6f5d2b5
Source dataset
uspto-grants-1996_06
Patent number
US05523411

Reaction notes

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