HCID 86702662, compound → HCID 86702661, compound

HRID 513328Notes

Reaction equation

HRID 513328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:15](=[O:17])[CH3:16]>[Au].ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:8]=[C:9]1[CH2:10][CH2:11][CH2:12][C:13]1=[C:14]2[C:15](=[O:17])[CH3:16]

Participants

4

Reactant 1

HCID 86702662HCID 86702662, compound

Product 1

HCID 86702661HCID 86702661, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

A microwave irradiation vial (10-20 mL) was equipped with a sir bar (1.5 cm) and was charged with compound 5c (0.20 g, 0.81 mmol) and 1,2-dichlorobenzene (13.5 mL). The reaction was irradiated with stirring at 180° C. for 3 h, turning gold in color. The solution was directly added to a silica gel column, which was eluted with n-hexane to separate the 1,2-dichlorobenzene and then AcOEt/n-hexane 1:9 to collect the pure product. The title compound was isolated as a yellow solid in a 86% yield (0.17 g).

Workup

  1. customA microwave irradiation vial (10-20 mL)
  2. customwas equipped with a sir bar (1.5 cm)
  3. customThe reaction was irradiated
  4. additionThe solution was directly added to a silica gel column, which
  5. washwas eluted with n-hexane
  6. customto separate the 1,2-dichlorobenzene
  7. customAcOEt/n-hexane 1:9 to collect the pure product

Sources & evidence

ORD record
ord-38183b1b705f4cf2b9d616ddfb184000
Source dataset
uspto-grants-2015_08
Patent number
US09102703B2

Reaction notes

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