Quinoline → HCID 53962161, compound

HRID 436871Notes

Reaction equation

HRID 436871 reaction equation
[OH:1][CH:2]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:3]#[C:4][CH2:5][CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].N1C2C(=CC=CC=2)C=CC=1.S([O-])([O-])(=O)=O.[Ba+2].[H][H]>C(OCC)(=O)C>[OH:1][CH:2]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:3]=[CH:4][CH2:5][CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 7047QuinolineHCID 24414Barium SulfateHCID 21431680HCID 21431680, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53962161HCID 53962161, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 10 g of the product of Step A in 50 ml of ethyl acetate containing 1 ml of quinoline was added to a suspension of 1 g of 50% palladized barium sulfate in 50 ml of ethyl acetate and the mixture was stirred in a hydrogen atmosphere until absorption ceased. The catalyst was removed by filtration and the filtrate was washed with dilute hydrochloric acid and water, dried over magnesium sulfate and evaporated. The residue was chromatographed over silica and was eluted with an 8-2 mixture of methylene chloride-ethyl acetate to obtain 6 g of ethyl 8-hydroxy-3-oxo-6-tetradecenoate in the form of a pale yellow oil with a refractive index of nD23 = 1.4602.

Workup

  1. customThe catalyst was removed by filtration
  2. washthe filtrate was washed with dilute hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed over silica
  6. washwas eluted with an 8-2 mixture of methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-09e5f20f2bd244dcad3de6dfa32b481f
Source dataset
uspto-grants-1977_06
Patent number
US04028386

Reaction notes

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