Réaction #54676

Équation de réaction

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

Solvants

tetrahydrofuran

THF

Conditions de réaction

Traitement

1. 1
   AutreThis compound was prepared
2. 2
   workup.ADDITIONInto a dry, nitrogen filled
3. 3
   Autreone liter 3-neck flask fitted
4. 4
   Températurewith reflux condenser
5. 5
   Autreserum cap
6. 6
   Températureto maintain gently
7. 7
   Températurereflux
8. 8
   workup.ADDITIONwas added to the warm reaction mixture at a rate sufficient
9. 9
   Températureto maintain gentle refluxing
10. 10
    TempératureThe reaction mixture was cooled in an ice-bath
11. 11
    workup.ADDITION600 ml of a 1:1 etherbenzene was added
12. 12
    AutreThe organic layer was separated
13. 13
    Extractionthe aqueous phase was extracted with ether
14. 14
    LavageThe combined extracts were washed with water (2×100 ml)
15. 15
    Séchagedried (MgSO4)
16. 16
    AutreRemoval of the solvent
17. 17
    Autreby evaporation

Mode opératoire

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).

Source