Methane, dichloromethoxy- → 1-Ethyl-5-formyloxindole

HRID 1788946Notes

Reaction equation

HRID 1788946 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:12])[CH3:2].[CH3:13][O:14]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:13]=[O:14])=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:12])[CH3:2]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-2×HCID 66135N-Ethyloxindole

Product 1

HCID 137705221-Ethyl-5-formyloxindoleYield 76%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 32.2 g. (0.2 mole) of 1-ethyloxindole in 200 ml. of methylene chloride was added 44 ml. (0.4 mole) of titanium tetrachloride followed by 22.6 ml. (0.25 mole) of dichloromethyl methyl ether. The reaction was stirred for 10.5 days at 25° C. followed by the addition of additional titanium tetrachloride and dichloromethyl methyl ether every 48 hours. The reaction was poured onto 1 l. of ice and water and extracted with methylene chloride. Concentration of the dried extract gave the crude product which was recrystallized from diethyl ether, 28.6 g. (76% yield), m.p. 126°-127° C.

Workup

  1. additionThe reaction was poured onto 1 l
  2. extractionof ice and water and extracted with methylene chloride
  3. extractionConcentration of the dried extract

Sources & evidence

ORD record
ord-de8eb938f854499db8dc033cab51fe90
Source dataset
uspto-grants-1987_08
Patent number
US04686224

Reaction notes

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