HCID 86702675, compound → HCID 86702674, compound

HRID 513340Notes

Reaction equation

HRID 513340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][CH2:10][C:11]([CH2:22][C:23]#[C:24][C:25](=[O:27])[CH3:26])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>[Au].ClC1C=CC=CC=1Cl>[C:25]([C:24]1[C:4]2[C:3](=[C:2]([Cl:1])[CH:7]=[CH:6][CH:5]=2)[CH:8]=[C:9]2[CH2:10][C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:22][C:23]=12)(=[O:27])[CH3:26]

Participants

4

Reactant 1

HCID 86702675HCID 86702675, compound

Product 1

HCID 86702674HCID 86702674, compound

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 5m (0.3 g, 0.77 mmol) and 1,2-dichlorobenzene (12.8 mL). The reaction was irradiated with stirring at 180° C. for 30 min, turning gold in color. The reaction 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 2:8 to collect the pure product. The title compound was isolated as a yellow oil in quant. yield (0.298 g). Small traces of contaminants were observed.

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 reaction 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 2:8 to collect the pure product

Sources & evidence

ORD record
ord-202a1936186b4eecbc13155b33fd8ead
Source dataset
uspto-grants-2015_08
Patent number
US09102703B2

Reaction notes

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