Thiophenol → 2-[1-(2-phenylthioethyl)cyclopropyloxy]tetrahydro-4H-pyran

HRID 1591053Notes

Reaction equation

HRID 1591053 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH2:15][CH2:14]2)(=O)=O)=CC=1.CC(C)([O-])C.[K+].[C:30]1([SH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[C:30]1([S:36][CH2:11][CH2:12][C:13]2([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[CH2:14][CH2:15]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 197661232-[1-(2-p-Toluenesulphonyloxyethyl)cyclopropyloxy]tetrahydro-4H-pyran2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 197661132-[1-(2-phenylthioethyl)cyclopropyloxy]tetrahydro-4H-pyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[1-(2-p-Toluenesulphonyloxyethyl)cyclopropyloxy]tetrahydro-4H-pyran (Compound 4) (1.30 g) was dissolved in a premixed, stirred solution of potassium tert-butoxide (0.45 g) and thiophenol (0.50 g) in N,N-dimethylformamide (10 ml) at room temperature. After a few minutes a precipitate started forming, and after 30 minutes the mixture was partitioned between ether (50 ml) and water. The organic layer was washed consecutively with 2N sodium hydroxide solution, water, and brine. Drying and concentration in vacuo gave a residue which was purified by chromatography (50 g silica gel; 10% ether in petroleum ether as eluant) to give 2-[1-(2-phenylthioethyl)cyclopropyloxy]tetrahydro-4H-pyran. Distillation of a portion gave an analytical sample, b.p. 121°-122° C./0.1 mmHg. (Found: C, 69.07; H, 8.01; S, 11.31. C16H22O2S requires C, 69.03; H, 7.97; S, 11.52%).

Workup

  1. customAfter a few minutes a precipitate started forming
  2. customafter 30 minutes the mixture was partitioned between ether (50 ml) and water
  3. washThe organic layer was washed consecutively with 2N sodium hydroxide solution, water, and brine
  4. customDrying
  5. concentrationconcentration in vacuo
  6. customgave a residue which
  7. customwas purified by chromatography (50 g silica gel; 10% ether in petroleum ether as eluant)

Sources & evidence

ORD record
ord-3b5a6e2d969247219b220465fcc331bc
Source dataset
uspto-grants-1993_04
Patent number
US05206229

Reaction notes

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