Tetrahydrofuran → HCID 178459255, compound

HRID 1968947Notes

Reaction equation

HRID 1968947 reaction equation
[CH2:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([O:13]CC)=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH3:3].[OH-].[Na+].O1CCCC1>CO>[CH2:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178459257HCID 178459257, compound

Product 1

HCID 178459255HCID 178459255, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

cis/trans-Ethyl 4-(propyloxy)cyclohexanecarboxylate (D11) (39.1 g), 40% w/w sodium hydroxide solution (150 mL), tetrahydrofuran (200 mL) and methanol (150 mL) was stirred for approx. 72 hours. The solvent was partially removed then the resulting mixture was treated with ethyl acetate and water. The aqueous layer was separated, acidified with concentrated hydrochloric acid and extracted with diethyl ether. The ether layer was washed with brine, dried with anhydrous sodium sulphate and the solvent was removed to give the title compounds as oil (15.42 g).

Workup

  1. customThe solvent was partially removed
  2. additionthe resulting mixture was treated with ethyl acetate and water
  3. customThe aqueous layer was separated
  4. extractionextracted with diethyl ether
  5. washThe ether layer was washed with brine
  6. dry with materialdried with anhydrous sodium sulphate
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-262802e0c8db4176898cb42d231e0574
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

Loading…