Tetrahydrofuran → HCID 69759935, compound

HRID 1860302Notes

Reaction equation

HRID 1860302 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][C:20]3[C:19]([CH3:23])([CH3:22])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH2:14]2)=[CH:7][CH:6]=1)C.[OH-].[K+].C1COCC1>C(O)C.O>[CH3:23][C:19]1([CH3:22])[CH2:18][CH2:17][C:16]([CH3:24])([CH3:25])[C:15]2[CH2:14][C:13]([CH:12]=[CH:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:31])=[O:3])=[CH:10][CH:9]=3)([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][C:20]1=2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 69760958HCID 69760958, compound

Product 1

HCID 69759935HCID 69759935, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The ester (0.7 g) was dissolved in 10 ml of ethanol and treated with a solution of 1.8 g of KOH in 5 ml of water. After having added 4 ml of THF, the reaction mixture was reacted for 3 hours at 40° C., poured on ice/water, acidified with 2N HCL and extracted with ethyl acetate. The organic phase was dried (Na2SO4), the solvent evaporated, and the crystalline residue recrystallized from pentane to give 0.4 g of 4-[2-(4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-yl)-vinyl]-benzoic acid as colorless crystals, m.p. 121-123° C.

Workup

  1. customthe reaction mixture was reacted for 3 hours at 40° C.
  2. additionpoured on ice/water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent evaporated
  6. customthe crystalline residue recrystallized from pentane

Sources & evidence

ORD record
ord-1783f77dc329402093766baa96985a51
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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