Ethylene Oxide → Ethylene Oxide

HRID 1656272Notes

Reaction equation

HRID 1656272 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH2:13]1[O:15][CH2:14]1>CS(C)=O>[CH2:14]1[O:15][CH2:13]1.[OH:15][CH2:14][CH2:13][N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

6

Reactant 3

HCID 6354Ethylene OxideHCID 14798Sodium HydroxideHCID 249055-Bromoindole

Product 2

HCID 6354Ethylene OxideHCID 106576502-(5-Bromo-1H-indol-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of NaOH (4.4 gm, 0.011 mol) in DMSO (175 ml) was stirred at 100° C. for 5 hours at which time it was cooled to 20° C. To this mixture was added 5-bromoindole (20 gm, 0.102 mol) and the reaction was stirred for 8 hours at room temperature. A solution of ethylene oxide (5.1 gm, 0.125 mol) in DMSO (20 ml) was prepared by bubbling the gas into DMSO. To the bromoindole reaction mixture was slowly added the ethylene oxide solution and stirring was continued for another 2.5 hours. The reaction mixture was then poured into ice water and extracted twice with diethyl ether. The combined ether extracts were concentrated in vacuo whereupon crystallization took place. The crude product was recrystallized from diethyl ether:hexanes (3:2) to afford the title compound (6.25 gm).

Workup

  1. temperaturewas cooled to 20° C
  2. stirringthe reaction was stirred for 8 hours at room temperature
  3. customby bubbling the gas into DMSO
  4. customTo the bromoindole reaction mixture
  5. stirringstirring
  6. waitwas continued for another 2.5 hours
  7. extractionextracted twice with diethyl ether
  8. concentrationThe combined ether extracts were concentrated in vacuo whereupon crystallization
  9. customThe crude product was recrystallized from diethyl ether:hexanes (3:2)

Sources & evidence

ORD record
ord-15ffd5ed3f20407b840d069a25087daf
Source dataset
uspto-grants-1993_10
Patent number
US05252732

Reaction notes

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