Background and overview[1]
3,3-Diphenylpropyl-2-propen-1-ol can be used as a pharmaceutical synthesis intermediate. Traditionally, carbonyl compounds are reduced to the corresponding alcohols through stoichiometric reduction of hydrides such as NaBH4, LiAlH4, or metal catalysts catalyze the reaction of carbonyl compounds and hydrogen. to achieve. However, these reagents have many shortcomings. NaBH4 and LiAlH4 are sensitive to air and moisture. Using hydrogen as a hydrogen source requires more demanding equipment and technology. If you inhale 3,3-diphenylpropyl-2-propen-1-ol, a commonly used antioxidant, please move the patient to fresh air; if there is skin contact, take off contaminated clothing and wash thoroughly with soap and water. Rinse the skin and seek medical attention if you feel discomfort. If contact occurs with eyes, separate eyelids, rinse with running water or saline, and seek medical attention immediately. If ingested, rinse mouth immediately. Do not induce vomiting and seek medical attention immediately.
Preparation[1]
3,3-Diphenylpropyl-2-propen-1-ol is prepared as follows: 4-[2-phenylvinyl]acetophenone (1mmol), NaOH (20mol%) and [Cu6(dmpymt)6] (1.67 mol%) was added to a dry reflux reaction tube equipped with a magnetic stirrer, and then anhydrous isopropyl alcohol (2 mL) was added. Then, the reaction tube was replaced with N2 three times, and the reaction was stirred at 100°C for 24 hours. After the reaction, the solution was cooled to room temperature, 5 mL of water was added, and then extracted with 3×5 mL of ethyl acetate. The organic phases were combined, and the organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by rotary evaporation and separated by silica gel column chromatography to obtain The target product 3,3-diphenylpropyl-2-propen-1-ol (yield 91%).
Nuclear magnetic spectrum analysis data of the obtained catalytic product: ΉNMR (MHz, DMSO-d6) δ7.59 (d, J=7.6Hz, 2H), 7.55 (d, /=7.9Hz , 2H), 7.36 (dd, / = 15.7, 7.8Hz, 4H), 7.30-7.20 (m, 3H), 5.16 (d, / = 4.1Hz, IH), 4.73 (dd, / = 10.8, 5.6Hz, IH), 1.32 (d, /=6.4Hz, 3H).13CNMR (151MHz, DMSO-d6) δ147.4, 137.5, 135.8, 129.1, 128.7 , 128.1, 127.9, 126.8, 126.6, 126.1, 68 free silica.3, 26.3.
Main reference materials
[1] WO2018148950 Application of 4,6-dimethyl-2-mercaptopyrimidine monovalent copper complex in catalyzing the hydrogen transfer reaction of ketones or aldehydes to prepare alcohols
