Tetrahydrofuran → Ethylene Oxide

HRID 1380296Notes

Reaction equation

HRID 1380296 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C([Li])CCC.C1C[O:29][CH2:28][CH2:27]1>CCCCCC>[CH2:11]1[O:20][CH2:12]1.[CH3:1][C:2]1[N:3]([CH2:27][CH2:28][OH:29])[C:4]2[C:9]([C:10]=1[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 10422724HCID 10422724, compoundHCID 178418339Butyllithium

Product 2

HCID 6354Ethylene OxideHCID 13755396HCID 13755396, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following a procedure similar to that described in Preparation 7A above, 9.75 g. (0.0375 mole) of 2-methyl-3-(4-cyanobenzoyl)indole (Preparation 1T) in 125 ml. of THF was treated with 16.65 ml. (0.04 mole) of a 2.4M solution of n-butyl lithium in hexane followed by 11.4 ml. of a 3.5M solution of ethylene oxide in THF to give 2-methyl-3-(4-cyanobenzoyl)-1-(2-hydroxyethyl)-1H-indole. Reaction of 30.4 g. (0.1 mole) of the latter with 21.0 g. (0.11 mole) of p-toluenesulfonyl chloride in 50 ml. of methylene dichloride in the presence of 50 ml. of 35% sodium hydroxide and 0.91 g. (0.004 mole) of benzyl trimethylammonium chloride afforded 38.3 g. (84%) of 2-methyl-3-(4-cyanobenzoyl)-1-(2-p-toluenesulfonyloxyethyl)-1H-indole, m.p. 165°-167° C.

Sources & evidence

ORD record
ord-a269d3b899e543eb80a0e8d66d5165b9
Source dataset
uspto-grants-1986_04
Patent number
US04581354

Reaction notes

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