Sodium Hydroxide → HCID 23001102, compound

HRID 2110982Notes

Reaction equation

HRID 2110982 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]1[CH:17]([C:18]([O:20]CC)=[O:19])[CH:12]1[CH2:11][CH2:10]2)(C)C.[OH-].[Na+]>CO.O>[C:6]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]1[CH:17]([C:18]([OH:20])=[O:19])[CH:12]1[CH2:11][CH2:10]2)#[CH:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23001113HCID 23001113, compound

Product 1

HCID 23001102HCID 23001102, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 5-[(trimethylsilyl)ethynyl]-1a,2,3,7b-tetrahydro-1-H-cyclopropa[a]naphthalene-1-carboxylate (0.2 g, 0.64 mmol) was dissolved in 4 ml of methanol and the solution of sodium hydroxide (0.05 g, 1.2 mmol) in 2 ml of water was added to the reaction mixture and stirred at heating at 65° C. for 6 h. The extraction of basic reaction mixture into hexane showed that no starting material present. The reaction mixture was acidified with excess of 3M HCl solution (pH=1), and extracted into ethylacetate (3×15 ml). The combined extracts were washed with water and brine, dried over Na2SO4 and concentrated by rotary evaporation to give 0.12 g of mixture of cis/trans acids (85:15) as white solid. Yield 88%. 7

Workup

  1. extractionThe extraction of basic reaction mixture into hexane
  2. extractionextracted into ethylacetate (3×15 ml)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ed85ced6fd574436aee89e1f818c5591
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

Loading…