Water → HCID 68497085, compound

HRID 444731Notes

Reaction equation

HRID 444731 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1.C(OCC)(=O)C.O>O1CCCC1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH:11]=[C:10]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH2:9][OH:8])[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 68492947HCID 68492947, compound

Product 1

HCID 68497085HCID 68497085, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 mL round bottom flask lithium aluminium hydride WAIN (0.28 g, 7.2 mmol) in tetrahydrofuran (THF) was taken and cooled to 0-5° C., to which methyl-3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-enoate (2 g, 6.09 mmol) dissolved in THF (15 mL) was added drop wise using dropping funnel. The reaction mixture was stirred for 1 hour at same temperature and the reaction was monitored by TLC. Upon the completion of reaction, added ethyl acetate (50 mL) drop wise followed by cold water (50 mL). The organic layer was separated and the aqueous layer further extracted with ethyl acetate (50 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give pure compound (1 g, 55%).

Workup

  1. additionwas added drop
  2. customUpon the completion of reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer further extracted with ethyl acetate (50 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04d5e641fd6742b29dddb560d9b85bd5
Source dataset
uspto-grants-2013_07
Patent number
US08476255B2

Reaction notes

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