Lithium Hydroxide → HCID 59180521, compound

HRID 1913776Notes

Reaction equation

HRID 1913776 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Li+]>C1COCC1.O.C(OCC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59180529HCID 59180529, compound

Product 1

HCID 59180521HCID 59180521, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 744 mg (1.75 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-methoxyphenyl)but-3-en-1-yl]benzoate in 24 ml of THF and 24 ml of water is mixed with 84 mg (3.5 mmol) of lithium hydroxide and stirred at 50° C. for 12 h. After conversion is complete, the reaction solution is diluted with diethyl ether and water, and the phases are separated. The aqueous phase is acidified with 1 M hydrochloric acid and extracted with diethyl ether. The resulting organic phase is washed with sodium chloride solution, dried over sodium sulphate and evaporated. 606 mg (1.5 mmol, 97% of theory) of the title compound are obtained.

Workup

  1. customthe phases are separated
  2. extractionextracted with diethyl ether
  3. washThe resulting organic phase is washed with sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-93d3b0f10bc0428baab1e76580906427
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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