Tetrahydrofuran → 6-Phenylsulfonyl-cis-tricos-14-ene

HRID 436935Notes

Reaction equation

HRID 436935 reaction equation
[CH2:1]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:28]([Li])[CH2:29][CH2:30][CH3:31].O1CCC[CH2:34]1>>[C:22]1([S:19]([CH:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:31][CH2:30][CH2:29][CH2:28][CH3:34])(=[O:21])=[O:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14681826OleylphenylsulfoneHCID 178418339Butyllithium

Product 1

HCID 146818286-Phenylsulfonyl-cis-tricos-14-eneYield 93%

Conditions

Temperature
-30 °C

Procedure

1.96 g (5.10- 3 mole) oleylphenylsulfone in solution in 10cm3 tetrahydrofuran are treated by the equivalent of butyl lithium at -78° C. The temperature is then allowed to rise progressively to 20° C. During this rise in temperature, the lithiated sulfone crystallises in the medium in the form of white crystals. The reaction mixture is once more cooled to -30° C. and 0.76 g (5.10-3 mole n. pentyl bromide in solution in 5 cm3 tetrahydrofuran are added thereto. After having kept the mixture at -30° C. for 10 minutes, the temperature is allowed to rise to 20° C. and stirring is continued for 2 hours. The reaction mixture is then hydrolyzed by a saturated aqueous solution of ammonium chloride and extracted three times with 50 cm3 ether. The combined ethereal extracts are washed three times with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated. 2.14 g (yield: 93%) of 6-phenylsulfonyl-cis-tricos-14-ene identified by thin layer chromatography and spectrography are thus obtained.

Workup

  1. customto rise progressively to 20° C
  2. customDuring this rise in temperature, the lithiated sulfone crystallises in the medium in the form of white crystals
  3. additionpentyl bromide in solution in 5 cm3 tetrahydrofuran are added
  4. customat -30° C.
  5. customfor 10 minutes
  6. customto rise to 20° C.
  7. extractionextracted three times with 50 cm3 ether
  8. washThe combined ethereal extracts are washed three times with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-46099d39295741f69c718567235215b1
Source dataset
uspto-grants-1977_06
Patent number
US04028422

Reaction notes

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