Propylene Oxide → HCID 86669535, compound

HRID 1184958Notes

Reaction equation

[CH:1]([NH:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH3:14])[C:7]=1[O:15][CH3:16])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]C(C)(C)C.[CH2:31]1[O:34][CH:32]1[CH3:33]>C1COCC1.CCCCCC.O>[OH:34][CH:32]([CH3:33])[CH2:31][C:11]1[C:6]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:17])=[C:7]([O:15][CH3:16])[C:8]([CH3:14])=[C:9]([O:12][CH3:13])[CH:10]=1

Participants

Conditions

Temperature: -15 °C

Procedure

4.74 g (20 mmol, 1 eq.) of amide (IX) and 6.1 mL (40 mmol, 2 eq.) of TMEDA are dissolved in 200 mL of THF in a dried round-bottomed flask under argon. The medium is then placed at −78° C. 33.9 mL (44 mmol, 2.2 eq.) of t-BuLi (1.3M as a solution in hexane) are then added and the solution is immediately warmed to −15° C. Once the red/orange coloration has appeared, the medium is cooled to −78° C. 1.43 mL (20 mmol, 1 eq.) of propylene oxide are then added dropwise. Once the addition is complete, the medium is warmed rapidly to −10° C. The solution is then slowly warmed to room temperature over 1 hour 30 minutes. A second addition of propylene oxide (1 eq.) is made if necessary (monitoring of the conversion by TLC). After 30 minutes, the reaction is hydrolyzed by addition of 100 mL of water.

Workup

customis then placed at −78° C
temperaturethe medium is cooled to −78° C
additionOnce the addition
temperaturethe medium is warmed rapidly to −10° C
temperatureThe solution is then slowly warmed to room temperature over 1 hour 30 minutes

Sources & evidence

ORD record: ord-da8f694031ff4545962a7c8b84bd25b9
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669378B2

Reaction notes

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