Citric Acid → HCID 15288606, compound

HRID 1757258Notes

Reaction equation

HRID 1757258 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C:3]#[C:4][C:5]#[C:6][CH2:7][CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH:31]=[CH:30][S:29][CH:28]=3)[CH:22]=2)[CH:14]=1)[C:9](O)=[O:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)C>[CH3:1][C:2]([CH3:33])([CH3:32])[C:3]#[C:4][C:5]#[C:6][CH2:7][CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH:31]=[CH:30][S:29][CH:28]=3)[CH:22]=2)[CH:14]=1)[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 19390150HCID 19390150, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15288606HCID 15288606, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

980 mg of (E)-2-(6,6-dimethyl-2,4-heptadiynyl)-3-[3-[2-[3-(3-thienyl)phenyl]ethenyl]phenyl]propionic acid is dissolved in 20 ml of ethyl ether, 132 mg of lithium aluminum hydride is added in several portions thereto under ice cooling and stirring, and the mixture is stirred at that temperature for 10 minutes. Saturated saline is added to the reaction solution to decompose the excessive reducing agent, and 20 ml of 10% aqueous citric acid solution and 30 ml of ethyl ether are added to form two liquid phases. The organic layer is taken, washed successively with 5% aqueous sodium bicarbonate solution and saturated saline, and dried over anhydrous sodium sulfate. The desiccating agent is filtered, the solvent is distilled off under reduced pressure, and the residue is crudely purified by silica gel short column chromatography [hexane/ethyl acetate=1/1] and then purified by medium pressure liquid chromatography [column: Lobar column, size B, Lichroprep Si 60 F (produced by Merck Co.); eluent: hexane/ethyl acetate=5/1→3/1 ] to obtain 625 mg (yield: 68%) of the captioned compound as a colorless oily matter.

Workup

  1. stirringthe mixture is stirred at that temperature for 10 minutes
  2. additionSaturated saline is added to the reaction solution
  3. additionare added
  4. customto form two liquid phases
  5. washwashed successively with 5% aqueous sodium bicarbonate solution and saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccating agent is filtered
  8. distillationthe solvent is distilled off under reduced pressure
  9. customthe residue is crudely purified by silica gel short column chromatography [hexane/ethyl acetate=1/1]
  10. custompurified by medium pressure liquid chromatography [column: Lobar column, size B, Lichroprep Si 60 F (produced by Merck Co.); eluent: hexane/ethyl acetate=5/1→3/1 ]

Sources & evidence

ORD record
ord-5f9d483c99e04f7b81ad40a3f04cf7df
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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