Lithium Hydroxide → HCID 21107185, compound

HRID 2377386Notes

Reaction equation

HRID 2377386 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[C:21]([CH:23]=[CH2:24])[C:20]3[C:19](=[O:25])[CH2:18][CH2:17][C:16]([CH3:27])([CH3:26])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Li+]>CO.O1CCCC1>[CH3:26][C:16]1([CH3:27])[C:15]2[CH:14]=[C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:28])=[O:2])=[CH:10][CH:9]=3)[CH:22]=[C:21]([CH:23]=[CH2:24])[C:20]=2[C:19](=[O:25])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57424239HCID 57424239, compound2×

Product 1

HCID 21107185HCID 21107185, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-(8,8-dimethyl-5-oxo-4-vinyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 70, 0.082 g, 0.22 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) was treated with a 2M solution of lithium hydroxide (1.5 mL, 3 mmol) and the resulting reaction mixture was stirred at ambient temperature for 1.5 h. The volatiles were evaporated in vacuo, the residue was neutralized with saturated aqueous ammonium chloride solution and extracted with diethyl ether and ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid (0.065 g, 82%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. extractionextracted with diethyl ether and ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-426f80d7edd4429c85588d42eaffe7c2
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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