6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde → 1-(6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanol

HRID 1582083Notes

Reaction equation

HRID 1582083 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][CH2:17][CH3:18])[CH2:9][CH2:8][C:7]2([CH3:20])[CH3:19])([CH3:3])[CH3:2].[CH3:21][Mg]Br>C1COCC1>[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH:14]([OH:15])[CH3:21])[CH:13]=1)[N:10]([CH2:16][CH2:17][CH3:18])[CH2:9][CH2:8][C:7]2([CH3:20])[CH3:19])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 867594426-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde2×HCID 178418573HCID 178418573, compound

Product 1

HCID 227198211-(6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, 6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde (Intermediate 8, 4.54 g, 19.2 mmol) and a solution of methyl magnesium bromide (3M, 16 ml, 47.9 mmol) in THF were reacted to give the title compound as a light yellow oil after purification by column chromatography using 5% ethyl acetate in hexane.

Sources & evidence

ORD record
ord-6b67bcb2ab5449c29983a9f3fa7ac79e
Source dataset
uspto-grants-2004_05
Patent number
US06734193B1

Reaction notes

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