Acetaldehyde → 1,2,3,4-Tetrahydro-alpha,1,4,4-tetramethyl-7-quinolinemethanol

HRID 373544Notes

Reaction equation

[Mg].Br[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:15])([CH3:14])[CH2:8][CH2:9][N:10]2[CH3:13])=[CH:5][CH:4]=1.[CH:16](=[O:18])[CH3:17]>O1CCCC1>[CH3:17][CH:16]([C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:15])([CH3:14])[CH2:8][CH2:9][N:10]2[CH3:13])=[CH:5][CH:4]=1)[OH:18]

Participants

Conditions

Temperature: 0 °C

Procedure

2 g of Magnesium shavings were covered with 20 ml of tetrahydrofuran. A solution of 20.8 g of 7-bromo-1,2,3,4-tetrahydro-1,4,4-trimethylquinoline in 80 ml of tetrahydrofuran was added dropwise thereto at 55°-60° C. using an ultrasonics bath. Thereafter, the mixture was boiled at reflux for an additional 2 hours, cooled to 0° C. and a solution of 10 g of acetaldehyde in 80 ml of tetrahydrofuran was added dropwise thereto. After stirring at room temperature for 1 hour, the mixture was poured on to ice/saturated ammonium chloride solution and extracted with ether. The oil obtained after drying and evaporation of the solvent was filtered over a silica gel column (eluting agent hexane/ethyl acetate 9:1) and gave 14.5 g of 1,2,3,4-tetrahydro-α,1,4,4-tetramethyl-7-quinolinemethanol as a yellowish oil.

Workup

customat 55°-60° C.
temperatureat reflux for an additional 2 hours
additionthe mixture was poured on to ice/saturated ammonium chloride solution
extractionextracted with ether
customThe oil obtained
customafter drying
customevaporation of the solvent
filtrationwas filtered over a silica gel column (eluting agent hexane/ethyl acetate 9:1)

Sources & evidence

ORD record: ord-d1e6f25332634f7d9418c5346fd63f48
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05164387

Reaction notes

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