Epichlorohydrin → {4-[(Oxiran-2-yl)methoxy]-1H-indol-6-yl}methanol
Reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.C[O-].[Na+]>>[O:17]1[CH2:16][CH:15]1[CH2:13][O:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2Participants
Procedure
3.3 g. of the 4-hydroxy-6-hydroxymethyl-indole thus prepared were dissolved in 30 ml. epichlorohydrin. To this solution were added dropwise, while stirring at ambient temperature, over the course of 1 hour, 20 ml. 2 N sodium methylate solution. After about 5 hours, the starting material had reacted. The solution was evaporated in a vacuum and the residue was mixed with water, as well as with a mixture of diethyl ether and ethyl acetate. The organic phase was shaken out several times with water, subsequently dried, treated with active charcoal and evaporated. The crude 4-(2,3-epoxypropoxy)-6-hydroxymethyl-indole thus obtained (about 5 g. of a brownish oil) contains, as by-product, some 4-(2-hydroxy-3-chloropropoxy)-6-hydroxymethyl-indole but was further used without further purification.
Workup
- dissolutionwere dissolved in 30 ml
- additionTo this solution were added dropwise
- waitAfter about 5 hours
- customthe starting material had reacted
- customThe solution was evaporated in a vacuum
- additionthe residue was mixed with water
- additionas well as with a mixture of diethyl ether and ethyl acetate
- stirringThe organic phase was shaken out several times with water
- customsubsequently dried
- additiontreated with active charcoal
- customevaporated
Sources & evidence
- ORD record
- ord-ea19f271b1224b87b99fa336fe76e431
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04229464
Reaction notes
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