2-Naphthalenethiol → HCID 85973476, compound

HRID 2245771Notes

Reaction equation

HRID 2245771 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8]Br.[CH:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[C:16]([SH:21])[CH:17]=[CH:18]2)=[CH:13][CH:12]=1.C(N(CC)CC)C>C(OCC)C>[CH3:1][O:2][C:3](=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][S:21][C:16]1[CH:17]=[CH:18][C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:20]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 70582-NaphthalenethiolHCID 8471TriethylamineHCID 54529347Methyl 6-bromohexa-2,4-dienoate

Product 1

HCID 85973476HCID 85973476, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6-bromo-hexa-2,4-dienoic acid methyl ester (1.57 g, 7.66 mmol) and 2-thionaphthol (1.35 g, 8.42 mmol) in diethyl ether (40 mL) was added dropwise triethylamine (1.40 mL, 10.0 mmol) under an atmosphere of argon. The mixture was stirred for one hour 20° C. and filtered. The filtrate was washed saturated aqueous sodium hydrogen carbonate (25 mL), demineralised water (25 mL) and brine (25 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a yellow oil that was purified by column chromatography (9:1 to 8:2 40-60° C. petroleum ether:diethyl ether). Recrystallisation from diethyl ether/petroleum ether afforded the title compound (1.9 g, 88%) as a white solid, mp 73-75° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed saturated aqueous sodium hydrogen carbonate (25 mL), demineralised water (25 mL) and brine (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow oil that
  7. customwas purified by column chromatography (9:1 to 8:2 40-60° C. petroleum ether:diethyl ether)
  8. customRecrystallisation from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-767484c515354748ba5be29eac4b0fab
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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