Diethyl Ether → 1-(Trimethylsilyloxy)-1-cyclohexyl-1-phenylhex-5-yn-2-one

HRID 1087657Notes

Reaction equation

[CH:1]([N-]C(C)C)([CH3:3])[CH3:2].[Li+].[CH3:9][Si:10]([CH3:29])([CH3:28])[O:11][C:12]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](=[O:15])[CH3:14].C(Br)C#C.CCOCC>C1COCC1>[CH3:29][Si:10]([CH3:28])([CH3:9])[O:11][C:12]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:13](=[O:15])[CH2:14][CH2:3][C:1]#[CH:2]

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium diisopropylamide is dissolved in dry THF and the solution cooled to -78° C. A solution containing 1-(trimethylsilyloxy)-1-cyclohexyl-1-phenylpropan-2-one in dry THF is added dropwise to the stirring solution at -78° C. After the addition is complete the reaction mixture is stirred for 1 hour. Then a solution of propargyl bromide in dry THF is added dropwise to the solution at -78° C. The solution is then warmed to 0° C. and stirred for 5 hours. An ether-acetic acid solution (9:1) is slowly added and the resultant mixture warmed to room temperature. Ether is added and the solution transferred to a separatory funnel and washed with water. The ether layer is dried over sodium sulfate and evaporated to dryness to afford the product as a white crystalline solid after recrystallization.

Workup

additionis added dropwise to the stirring solution at -78° C
additionAfter the addition
temperatureThe solution is then warmed to 0° C.
stirringstirred for 5 hours
customthe solution transferred to a separatory funnel
washwashed with water
dry with materialThe ether layer is dried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-6eefc7af85f440e2920cf7bb08a98786
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036107

Reaction notes

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