6-Isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde → 1-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-propan-1-ol

HRID 1582082Notes

Reaction equation

HRID 1582082 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH:14]=[O:15])[CH:13]=1)[N:10]([CH2:16][CH3:17])[CH2:9][CH2:8][C:7]2([CH3:19])[CH3:18])([CH3:3])[CH3:2].[CH2:20]([Mg]Br)[CH3:21]>C1COCC1>[CH2:16]([N:10]1[C:11]2[C:6](=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:13][C:12]=2[CH:14]([OH:15])[CH2:20][CH3:21])[C:7]([CH3:19])([CH3:18])[CH2:8][CH2:9]1)[CH3:17]

Participants

4

Reactant 2

HCID 227198126-Isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde2×HCID 178418443HCID 178418443, compound

Product 1

HCID 227198191-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, 6-isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde (Intermediate 7, 5.78 g, 26 mmol) and a solution of ethyl magnesium bromide (2M, 35 ml, 65 mmol) in THF were reacted to give the title compound as a yellow oil after purification by column chromatography using 5% ethyl acetate in hexane.

Sources & evidence

ORD record
ord-cdf630179c124caa86c26ac3bf720dab
Source dataset
uspto-grants-2004_05
Patent number
US06734193B1

Reaction notes

Loading…