Water → Methyl 1-methyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-6-indole carboxylate

HRID 256830Notes

Reaction equation

HRID 256830 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[NH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=4)[CH:5]=[CH:4][C:3]1=2.[H-].[Na+].[CH3:30]I.O>C1COCC1>[CH3:30][N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=2)[CH:22]=[C:14]1[C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:27])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13633596Methyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-6-indole carboxylate

Product 1

HCID 13633599Methyl 1-methyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-6-indole carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.40 g (3.8 mmol) of the ester produced in Example 13, are dissolved in 20 ml of dry THF, and treated with 0.14 g (4.6 mmol) of sodium hydride (80% in oil). This mixture is stirred for 1 hour, at which point 0.65 g (4.4 mmol) of methyl iodide is added. The resulting mixture is stirred for 2 hours and then poured into water (100 ml) and extracted with dichloromethane (3×100 ml). The organic phase is dried and the solvent evaporated. The resulting residue is recrystallized in hexane, yielding methyl 1-methyl-2-(5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthyl)-6-indole carboxylate. (1.30 g, 91%)

Workup

  1. additionis added
  2. extractionextracted with dichloromethane (3×100 ml)
  3. customThe organic phase is dried
  4. customthe solvent evaporated
  5. customThe resulting residue is recrystallized in hexane

Sources & evidence

ORD record
ord-c05ecdc5bde349e8ae40a88a4dbeeb70
Source dataset
uspto-grants-1993_11
Patent number
US05260295

Reaction notes

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