Toluene → 2-Hydroxymethyl-1-methyl-4,5,6-trimethoxyindole

HRID 720339Notes

Reaction equation

HRID 720339 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([O:15][CH3:16])[C:7]([O:13][CH3:14])=[C:8]([O:11][CH3:12])[CH:9]=2)[CH:4]=[C:3]1[C:17](OC)=[O:18].C1(C)C=CC=CC=1.C([Al]C(C)C)(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOCC>[OH:18][CH2:17][C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[C:6]([O:15][CH3:16])[C:7]([O:13][CH3:14])=[C:8]([O:11][CH3:12])[CH:9]=2

Participants

7

Reactant 4

HCID 1140TolueneHCID 62649Sodium sulfate decahydrateHCID 16687728DiisopropylaluminumHCID 21891561methyl N-methyl-4,5,6-trimethoxyindole-2-carboxylate

Product 1

HCID 218916442-Hydroxymethyl-1-methyl-4,5,6-trimethoxyindole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-methyl-4,5,6-trimethoxyindole-2-carboxylate (1.17 g) was dissolved in dry THF under an argon atmosphere at 0° C., a 1 M toluene solution (13.2 mL) of diisopropylaluminum bydride was added dropwise to the solution, and the mixture was stirred for 1 hour as it is. The reaction mixture was diluted with ether, the sodium sulfate decahydrate was added thereto, and the mixture was stirred further for 1 hour. After the reaction mixture was filtered, and the filtrate was concentrated, the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2 to 1:1) to obtain the title compound.

Workup

  1. stirringthe mixture was stirred further for 1 hour
  2. filtrationAfter the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2 to 1:1)

Sources & evidence

ORD record
ord-1b09fce2b55648cfa4333f6420440415
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

Loading…