p-Toluenesulfonic acid → Ethyl 4-[(5-acetoxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

HRID 53387Notes

Reaction equation

HRID 53387 reaction equation
[CH3:1][C:2]1([CH3:26])[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[C:5](=[O:25])[CH2:4][CH2:3]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:27]([O:25][C:5]1[C:6]2[CH:7]=[CH:8][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:10][C:11]=2[C:2]([CH3:1])([CH3:26])[CH2:3][CH:4]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 15345545Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate2×

Product 1

HCID 19962310Ethyl 4-[(5-acetoxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

Conditions

Temperature
80 °C

Procedure

To 200 mg (0.51 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonapth-2-yl)ethynyl]benzoate (Compound 1) was added 0.13 ml (1.5 mmol) of acetic anhydride and 10 mg (0.05 mmol) of p-toluenesulfonic acid. The mixture was heated at 80° C. for 12 hours, cooled to room temperature and concentrated in vacuo to an oil. Purification by flash chromatography (silica, 10% EtOAc-hexane) yielded the title compound as a light yellow powder.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo to an oil
  3. customPurification by flash chromatography (silica, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-3e05036fcc3340968a6d94747270326f
Source dataset
uspto-grants-1997_04
Patent number
US05618931

Reaction notes

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