Benzoyl Peroxide → Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-thioacetylnaphth-2-yl)ethynyl]benzoate

HRID 1242

Reaction equation

HRID 1242 reaction equation
[CH3:1][C:2]1([CH3:25])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:52]([O-])(=[S:54])[CH3:53].[K+]>C(Cl)(Cl)(Cl)Cl>[CH3:25][C:2]1([CH3:1])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:23][CH:24]=3)[CH:8]=[CH:7][C:6]=2[CH:5]([C:52](=[S:54])[CH3:53])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19694975Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate2×HCID 23670855Potassium ethanethioate

Product 1

HCID 19694969Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-thioacetylnaphth-2-yl)ethynyl]benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 543 mg (1.64 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (obtainable from Compound M by coupling with ethyl-4-iodobenzoate) in 20 ml of CCl4 was added 320 mg (1.81 mmol) of N-bromosuccinimide and 26 mg (0.11 mmol) of benzoyl peroxide. The mixture was refluxed for 3 hours under argon atmosphere, cooled, filtered through celite and concentrated in vacuo to a dark brown syrup. The syrup was taken up in 20 ml of dry THF and 780 mg (6.9 mmol) of potassium thioacetate was added. The mixture was refluxed for 4 hours under argon atmosphere, concentrated in vacuo and purified by chromatography (silica, 10% EtOAc-hexane) to yield the title compound as a pale yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 3 hours under argon atmosphere
  2. temperaturecooled
  3. filtrationfiltered through celite and
  4. concentrationconcentrated in vacuo to a dark brown syrup
  5. temperatureThe mixture was refluxed for 4 hours under argon atmosphere
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography (silica, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-a56f7e2293dc4862a8c854ae1b1ae4b3
Source dataset
uspto-grants-1998_03
Patent number
US05723620

Linked notes

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