Sodium Chloride → HCID 54151230, compound

HRID 6208Notes

Reaction equation

HRID 6208 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][C:17]([CH:21]=O)=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)(=O)C.[Br-].[O:24]1CCO[CH:25]1[CH2:29][P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+].[Cl-].[Na+]>CN(C)C=O.Cl.O>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][C:17]([CH:21]=[CH:29][CH:25]=[O:24])=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 22292430Tributyl(1,3-dioxolan-2-ylmethyl)phosphonium BromideHCID 23665647Potassium tert-butoxideHCID 54260784HCID 54260784, compound

Product 1

HCID 54151230HCID 54151230, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution 30.3 g (0.1 mole) of N-acetoxyhexyl-1,2,3,4-tetrahydroquinoline-6-carboxaldehyde in dimethylformamide is added 7.4 g (0.2 mole) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide with magnetic stirring, and the mixture is heated at 90° C. Potassium t-butoxide (22.4 g, 0.2 mole) is added, and heating is continued at 90° C. for 16 hours. After cooling to room temperature, the solution is poured into a seven-fold excess of water. The aqueous mixture is saturated with sodium chloride, and the mixture is extracted with three portions of ether. The combined organics are dried over 4A sieves, filtered through cotton, and evaporated. The crude reaction product is then dissolved in 3M HCl, and the reaction is stirred at room temperature for 16 hours. After careful neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether, and the combined organics are passed through silica gel, dried over 4A sieves, filtered through cotton, and evaporated to yield 3-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)acrolein.

Workup

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture is extracted with three portions of ether
  4. dry with materialThe combined organics are dried over 4A sieves
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customThe crude reaction product
  8. extractionAfter careful neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
  9. dry with materialdried over 4A sieves
  10. filtrationfiltered through cotton
  11. customevaporated

Sources & evidence

ORD record
ord-f11fb9357654407f897a52ae5b73be5e
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Reaction notes

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