HCID 86702665, compound → HCID 14909484, compound

HRID 2280058Notes

Reaction equation

HRID 2280058 reaction equation
[CH3:1][S:2]([C:5]#[C:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:4])=[O:3]>ClC1C=CC=CC=1Cl>[CH3:1][S:2]([C:5]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[C:10]2[CH2:9][CH2:8][CH2:7][C:6]=12)(=[O:3])=[O:4]

Participants

3

Reactant 1

HCID 86702665HCID 86702665, compound

Product 1

HCID 14909484HCID 14909484, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
225 °C

Procedure

To a 2-5 mL microwave irradiation vial equipped with a stir bar was added enyne 5f (0.050 g, 0.20 mmol) in o-dichlorobenzene (2.3 mL). The reaction was irradiated with stirring at 225° C. for 20 min until complete by TLC. The reaction turned golden in color. The crude product was purified by silica gel column chromatography (14 g silica cartridge, 0-15% ethyl acetate/hexanes) to yield naphthalene 6f as a colorless oil (0.038 g, 78%).

Workup

  1. customTo a 2-5 mL microwave irradiation
  2. customvial equipped with a stir bar
  3. customThe reaction was irradiated
  4. customThe crude product was purified by silica gel column chromatography (14 g silica cartridge, 0-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9984ac3b370d4bc99a0ded5cad98bb89
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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