2,3-Dimethyl-1,3-butadiene → 4-(4,5-Dimethylcyclohexa-1,4-dienyl)butan-1-ol

HRID 871107

Reaction equation

[CH3:1][C:2]([C:4]([CH3:6])=[CH2:5])=[CH2:3].[CH2:7]([OH:13])[CH2:8][CH2:9][CH2:10][C:11]#[CH:12]>C1COCC1.[Co](Br)Br.[I-].[Zn+2].[I-].[Zn].C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:3][C:2]1[CH2:1][CH:12]=[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][OH:13])[CH2:5][C:4]=1[CH3:6]

Participants

Conditions

Temperature: 70 °C

Procedure

In 40 mL of THF, 1,2-bis(diphenylphosphino)ethane (800 mg, 2.00 mmol), cobalt bromide (437 mg, 2.00 mmol), zinc iodide (1.28 g, 4.00 mmol), and zinc (260 mg, 4.00 mmol) were dissolved, followed by stirring at 70° C. for 15 minutes. After cooling to room temperature, 2,3-dimethyl-1,3-butadiene (9.86 g, 120 mmol) was added. Then, 5-hexyn-1-ol (9.8 g, 100 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35° C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 11.5 g of the title compound, an alcohol, was obtained as a colorless oily substance. Yield: 63.4%.

Workup

temperatureAfter cooling to room temperature
temperaturewith cooling in a water bath
stirringAfter stirring at 35° C. for 1 hour
customthe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-f0c857022204456ead7f1d293693c26b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969609B1

Linked notes

Loading…