Ethanol → HCID 15218978, compound

HRID 2209402Notes

Reaction equation

[CH2:1]([C:6]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[CH:14]=[N:15][C:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=3)=[N:17][CH:18]=2)=[C:8]([F:27])[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:28]([N-:31]C(C)C)(C)C.[Li+].C1(C)C=CC(S(C#N)(=O)=O)=CC=1.C(O)C>CCCCCC.C1COCC1>[CH2:1]([C:6]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([C:28]#[N:31])=[C:21]([F:26])[CH:20]=3)=[N:15][CH:14]=2)=[C:8]([F:27])[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: -50 °C

Procedure

A mixture of 44 mmol of 1B and 80 ml of THF is added dropwise at -78° C. to a solution of 48 mmol of lithium diisopropylamide in hexane. The mixture is stirred at -50° C. for 2 hours and then re-cooled to -78° C., and a mixture of 48 mmol of p-toluenesulphonyl cyanide in 20 ml of THF is slowly added dropwise. After warming to room temperature and conventional work-up, the pure product is obtained by recrystallization from ethanol. C 85 N (75) I, Δε=71.3, Δn=0.232 (extrapolated from ZLI-4792)

Workup

temperaturere-cooled to -78° C.
additionis slowly added dropwise
temperatureAfter warming to room temperature

Sources & evidence

ORD record: ord-defbbbb8bc5a4d2994bd0f6b8eb4d3f2
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05454975

Reaction notes

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