Dimethyl Sulfate → 7-Benzyloxy-1-methylindole

HRID 1822975Notes

Reaction equation

HRID 1822975 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+].S(OC)(O[CH3:31])(=O)=O>C(O)C.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[N:16]([CH3:31])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 2607987-(Benzyloxy)-1H-indole

Product 1

HCID 221368137-Benzyloxy-1-methylindole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-benzyloxy-1H-indole (Ref: Dobson, D; Todd, A; Gilmore, J. Synth. Commun. (1991), 21(5), 611–17) (1.29 g, 5.78 mmol) in ethanol (30 mL) was added potassium hydroxide (0.41 g, 7.23 mmol) and dichloromethane (5 mL) of to help solubilize the starting material. The resulting solution was allowed to stir at room temperature for 10 min before evaporating the solvent in vacuo. The residue was taken up in acetone (75 mL) and sodium sulfate (4.9 g, 34.7 mmol) was added followed by dimethyl sulfate via syringe (0.62 mL, 6.3 mmol). The solution was stirred for 1 h, then filtered and evaporated in vacuo. This material was purified by flash chromatography, eluting silica gel with hexane:ethyl acetate (100:0 to 10:1) to give the product. (1.12 g, 82%); Mass spectrum (ion spray): m/z=238.1 (M+1).

Workup

  1. custombefore evaporating the solvent in vacuo
  2. stirringThe solution was stirred for 1 h
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThis material was purified by flash chromatography
  6. washeluting silica gel with hexane:ethyl acetate (100:0 to 10:1)
  7. customto give the product

Sources & evidence

ORD record
ord-d1b5b587a6064d939230bcb2f5daf8ef
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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