Sodium hydride → HCID 10986718, compound

HRID 259824Notes

Reaction equation

HRID 259824 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:2].[H-].[Na+].[I-].[CH3:15][C:16](C)=C[SH2+]>C1COCC1>[O:2]1[CH:15]2[CH2:16][N:4]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=4[CH:11]=[C:3]3[CH:1]12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96389Indole-2-carboxaldehydeHCID 86749533HCID 86749533, compound

Product 1

HCID 10986718HCID 10986718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100-mL round-bottom flask, a total of 626 mg (4.31 mmol) of 2-formylindole and 259 mg (8.63 mmol) of NaH (80% dispersion in mineral oil) was stirred in 50 mL of dry THF under N2 at 0° C. ice bath). A total of 935 mg (4.31 mmol) of dimethylvinylsulfonium iodide was added after 20 minutes and the reaction mixture was stirred overnight (about 15 hours). The mixture was then evaporated under reduced pressure and the residue was washed with pentane or hexane. The filtrate was evaporated under reduced pressure. The resulting solid was analyzed by GC-MS and had a purity of 99%. Yield: 665 mg (72%). 1H NMR (CDCl3): δ4.09 (dd, 1H, J1 =12), 4.33 (d, 1H, J=12), 4.40 (d, 1H, J=2.5), 4.50 (t, 1H, J=2.5), 6.59 (s, 1H), 0.0-7.3 (m, 3H), 7.60 (d, 1H, J=7.5), 13C NMR (CDCl3 : δ45.94, 51.35, 60.83, 97.62, 109.23, 119.64, 121.68, 122.34, 131.44, 133.90, 139.12, MS (EI): m/z 171 (M+).

Workup

  1. customThe mixture was then evaporated under reduced pressure
  2. washthe residue was washed with pentane or hexane
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6fa4b25b7c5344f8aeeb9e05e197554c
Source dataset
uspto-grants-1996_06
Patent number
US05523411

Reaction notes

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