Dimethyl oxalate → 7-Benzyloxy-1-methylindole

HRID 1826990

Reaction equation

HRID 1826990 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3]1.[CH2:12](OC1C=CC=C2C=1NC=C2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OC)(=O)C(OC)=O.CC(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:12]([O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:2]([CH3:1])[CH:3]=[CH:4]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 11120Dimethyl oxalateHCID 2607987-(Benzyloxy)-1H-indoleHCID 516892Sodium BicarbonateHCID 221368021-methyl-1H-indol-7-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 221368137-Benzyloxy-1-methylindole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

1-Methyl-indol-7-ol: A mixture of 7-benzyloxyindole (300 mg, 1.34 mmol), dimethyl oxalate (317 mg, 2.68 mmol) and potassium tert-butoxide (302 mg, 2.68 mmol) in 5 mL DMF was stirred at 110° C. overnight. The solution was poured into NaHCO3 saturated solution (20 mL) and extracted with EtOAc. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent was removed in vacuo to yield 200 mg of 7-benzyloxy-1-methylindole, which was hydrogenated by 5% Pd/C in 20 mL methanol under H2 (50 psi) to yield 90 mg (45.5%) of the title compound. 1H NMR (CDCl3): 7.19–7.16 (m, 1H), 6.94 (d, J=3 Hz, 1H), 6.86 (t, J=7.5 Hz, 1H), 6.48–6.46 (m, 1H), 6.40 (d, J=3 Hz, 1H), 5.05 (s, 1H), 4.07 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-35e34d7e070f47b8a7d4bdd0f163d079
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Linked notes

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