Sodium sulfate decahydrate → 287384-86-5

HRID 392089Notes

Reaction equation

HRID 392089 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:20](OCC)=O)[N:14]2[CH2:17][C:18]#[N:19])=[CH:10][CH:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:12]=[C:13]3[CH2:20][NH:19][CH2:18][CH2:17][N:14]3[C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 21868767HCID 21868767, compound

Product 1

HCID 21868746287384-86-5Yield 28.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of lithium aluminium hydride (0.16 g, 4.2 mmol) in ether (20 mL) at 0° C. under Ar was added ethyl 6-chloro1-(cyanomethyl)-7-azaindole-2-carboxylate (0.45 g, 1.7 mmol). The mixture was heated under refux for 18 h, cooled to room temperature and treated with sodium sulfate decahydrate (2.8 g, 8.4 mmol). The mixture was stirred for 30 min, filtered through kieselguhr, concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-methanol (9:1)] to give the product as a yellow oil (0.10 g, 27%). IR νmax (Nujol)/cm−1 3230, 2925, 2855, 1594, 1561, 1528, 1466, 1429, 1397, 1342, 1306, 1257, 1121, 1100, 1022, 948, 901, 874, 822, 810, 746, 546 and 509; NMR δH (400 MHz, CDCl3), 3.31 (2H, t, J 6 Hz), 4.15 (2H, t, J 6 Hz), 4.19(2H, s), 6.11 (1H, s), 7.03 (1H, d, J 8 Hz), 7.72 (1H, d, J 8 Hz).

Workup

  1. temperatureThe mixture was heated under refux for 18 h
  2. filtrationfiltered through kieselguhr
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography [SiO2; ethyl acetate-methanol (9:1)]

Sources & evidence

ORD record
ord-66e6d7fa3c5343d1bdc0da601ae2748e
Source dataset
uspto-grants-2004_10
Patent number
US06800627B1

Reaction notes

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