Reaktion #54676

Reaktionsgleichung

3-methyl-1,2,4,5-tetrahydro-3H-benz[e]indole

bromochloroethan

isopropyl magnesium chloride

ethylenediaminetetraacetic acid tetrasodium salt

→

oxygen

3-Cyclopropylmethyl-8-methoxy-1,2,4,5-tetrahydro-3H-benz[e]indole

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was prepared
2. 2
   workup.ADDITIONInto a dry, nitrogen filled
3. 3
   Sonstigeone liter 3-neck flask fitted
4. 4
   Temperaturwith reflux condenser
5. 5
   Sonstigeserum cap
6. 6
   Temperaturto maintain gently
7. 7
   Temperaturreflux
8. 8
   workup.ADDITIONwas added to the warm reaction mixture at a rate sufficient
9. 9
   Temperaturto maintain gentle refluxing
10. 10
    TemperaturThe reaction mixture was cooled in an ice-bath
11. 11
    workup.ADDITION600 ml of a 1:1 etherbenzene was added
12. 12
    SonstigeThe organic layer was separated
13. 13
    Extraktionthe aqueous phase was extracted with ether
14. 14
    WaschenThe combined extracts were washed with water (2×100 ml)
15. 15
    Trocknendried (MgSO4)
16. 16
    SonstigeRemoval of the solvent
17. 17
    Sonstigeby evaporation

Vorschrift

This compound was prepared according to the procedure described by Evans, et al., J. Org. Chem. 35, 4122 (1970) for the synthesis of 3-methyl-1,2,4,5-tetrahydro-3H-benz[e]indole as follows. Into a dry, nitrogen filled, one liter 3-neck flask fitted with reflux condenser, serum cap, dropping funnel and magnetic stirrer, was added a solution of 38.55 g (167.9 mmol) XIIa in dry tetrahydrofuran (THF) (50 ml) which was placed under a slow stream of nitrogen. A 2.20 M solution of isopropyl magnesium chloride in THF (96.1 ml, 211.7 mmol) was added slowly via a syringe at such a rate as to maintain gently reflux. After the addition (15 min), 30.72 g (214.2 mmol) of bromochloroethan was added to the warm reaction mixture at a rate sufficient to maintain gentle refluxing. After the addition of the alkylhalide, an additional 52.3 ml (115 mmol) of the Grignard reagent was added to the reaction again at a controlled rate. The reaction mixture was cooled in an ice-bath and 270 ml of 1 M aqueous solution of ethylenediaminetetraacetic acid tetrasodium salt was added slowly (with stirring) and then 600 ml of a 1:1 etherbenzene was added. The organic layer was separated and the aqueous phase was extracted with ether. The combined extracts were washed with water (2×100 ml) and dried (MgSO4). Removal of the solvent by evaporation gave 43.0 g (99%) of XIIIa as a pale yellow oxygen-sensitive oil; IR (neat), 1635 cm-1 (C=C--N).

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