Potassium Hydroxide → HCID 68722407, compound

HRID 1471388Notes

Reaction equation

HRID 1471388 reaction equation
[OH-].[K+].[CH3:3][C@H:4]1[CH2:13][CH:12]=[CH:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[C@H:5]1[C:14]([O:16]CC)=[O:15].[OH-].[Na+]>C(O)C>[CH3:3][CH:4]1[CH2:13][CH:12]=[CH:11][C:6]2([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH:5]1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 68769890HCID 68769890, compound

Product 1

HCID 68722407HCID 68722407, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of KOH (19.1 g, 289 mmol) in ethanol (60 ml) was treated with rel-(6S,7S)-ethyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate (4.28 g, 19.2 mmol, prepared as described in Example 19) and after refluxing for 3 d, the resulting mixture was poured into cold 2N aqueous NaOH (100 ml), and extracted twice with cyclohexane (50 ml). The combined aqueous phases were acidified with conc. HCl, extracted twice with MTBE (50 ml), and the combined org. phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4), and concentrated. FC (300 g SiO2, hexane/MTBE 8:1) of the crude product (2.65 g) gave 7-methylspiro[4.5]dec-9-ene-6-carboxylic acid (1.4 g, 37%).

Workup

  1. temperatureafter refluxing for 3 d
  2. extractionextracted twice with cyclohexane (50 ml)
  3. extractionextracted twice with MTBE (50 ml)
  4. washphases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53afdbbe1f46429ca862a3d1b022b138
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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