Ethanol → HCID 9815537, compound

HRID 568207Notes

Reaction equation

HRID 568207 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C:7]([CH3:19])([O:13]C1CCCO1)[C:8]#[C:9][CH:10]1[CH2:12][CH2:11]1)[CH3:3].C(O)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C[O-].[Na+]>O>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C:7]([CH3:19])([OH:13])[C:8]#[C:9][CH:10]1[CH2:12][CH2:11]1)[CH3:1]

Participants

6

Reactant 4

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 9816749HCID 9816749, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 9815537HCID 9815537, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a dried flask (300 ml volume), the inside of which had been flushed with nitrogen, were placed 2,6-dimethyl-6-tetrahydrofuranoxy-8-cyclopropyl-7-octyne (10.72 g, purity 98.5%, 0.04 mol.) prepared in Example 2, ethanol (100 ml) and pyridinium p-toluenesulfonate (5.4 mg). The resulting mixture was heated at 50° C. to 60° C. for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and to the mixture was added 10 mg of sodium methoxide (25% methanol solution). Ethanol was removed by distillation through a rotary evaporator. To the concentrate obtained was added 100 ml of water and the resulting mixture was subjected to extraction with two 100 ml portions of ethyl acetate. The extract was washed with an aqueous saturated sodium bicarbonate solution and a saturated saline solution, dried over anhydrous sodium sulfate and concentrated by distillation of the solvent through a rotary evaporator to give 10.1 g of a crude product. The crude product was purified by distillation under reduced pressure to give 2,6-dimethyl-6-hydroxy-8-cyclopropyl-7-octyne (7.33 g, purity 99.0%, yield 93.5%) having the following physical data:

Workup

  1. customIn a dried flask (300 ml volume), the inside of which had been flushed with nitrogen
  2. temperatureThe resulting mixture was heated at 50° C. to 60° C. for 2 hours
  3. customEthanol was removed by distillation through a rotary evaporator
  4. customTo the concentrate obtained
  5. extractionthe resulting mixture was subjected to extraction with two 100 ml portions of ethyl acetate
  6. washThe extract was washed with an aqueous saturated sodium bicarbonate solution
  7. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  8. concentrationconcentrated by distillation of the solvent through a rotary evaporator
  9. customto give 10.1 g of a crude product
  10. distillationThe crude product was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-2bcebdfeee69447db56dae9210239470
Source dataset
uspto-grants-2001_01
Patent number
US06180835B2

Reaction notes

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