Sodium sulfate decahydrate → 287384-86-5

HRID 857456Notes

Reaction equation

HRID 857456 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 aluminum hydride (0.16 g, 4.2 mmol) in ether (20 mL) at 0° C. under Ar was added ethyl 6-chloro-1-(cyanomethyl)-7-azaindole-2-carboxylate (0.45 g, 1.7 mmol). The mixture was heated under reflux 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 nun, 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 M 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
  2. temperatureunder reflux for 18 h
  3. filtrationfiltered through kieselguhr
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography [SiO2; ethyl acetate-methanol (9:1)]

Sources & evidence

ORD record
ord-13407c2d6fea473ebc7c9a979d2d178d
Source dataset
uspto-grants-2006_12
Patent number
US07145009B2

Reaction notes

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