Thiophenol → HCID 18790170, compound

HRID 1107108Notes

Reaction equation

HRID 1107108 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Li]CCCC>C1COCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 54541139t-Butyl 7-phenyl-2-heptenoateHCID 178418339Butyllithium

Product 1

HCID 18790170HCID 18790170, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

t-butyl 7-phenylhept-2-enoate (2 g; 7.7 mmol) and thiophenol (1.2 g; 11 mmol) are dissolved in THF (25 mL) and cooled to 0° C. n-BuLi (2.5 M in hexane; 0.3 mL; 0.7 mmol) is added dropwise and the reaction is allowed to warm and stir at 20° C. for 3 hours. The reaction is concentrated in vacuo and purified by column chromatography using 5% Et2O/petroleum ether to obtain t-butyl 7-phenyl-3-phenylsulfanylheptanoate.

Workup

  1. additionis added dropwise
  2. temperatureto warm
  3. concentrationThe reaction is concentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-9e54f8035b1d462ca88ebe87b2669bb2
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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