Lithium Hexamethyldisilazide → HCID 86629985, compound

HRID 1013799Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:30][C:31]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[C:34]([F:41])=[C:33]([F:42])[C:32]=1[CH2:43]I>C1COCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[C@H:15]([CH2:43][C:32]1[C:31]([Cl:30])=[CH:36][C:35]([C:37]([F:40])([F:38])[F:39])=[C:34]([F:41])[C:33]=1[F:42])[CH2:16][CH:17]=[CH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Cool a solution of (R)-4-Benzyl-3-pent-4-enoyl-oxazolidin-2-one (0.94 g, 3.6 mmol) in THF (10 mL) to −78° C. Treat this solution dropwise with 10M LiHMDS in THF (4 mL, 4.0 mmol) and stir at −78° C. for 30 minutes. Treat the solution with 1-Chloro-3,4-difluoro-2-iodomethyl-5-trifluoromethyl-benzene (1.35 g, 3.8 mmol) and allowed to slowly warm to room temperature. The reaction stirs 4 hr at room temperature. Quench the reaction with 1N HCl (aqueous) and extracted with Et2O. Wash the organic with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography using Hexanes:EtOAc to elute the pure product. Remove the solvent to afford 0.725 g (41%) of desired product. MS (m/e): 488 (M+1).

Workup

temperatureto slowly warm to room temperature
waitThe reaction stirs 4 hr at room temperature
customQuench
customthe reaction with 1N HCl (aqueous)
extractionextracted with Et2O
washWash the organic with brine
dry with materialdry over MgSO4
filtrationfilter
customremove the solvent
customPurify the crude by silica gel column chromatography
washEtOAc to elute the pure product
customRemove the solvent

Sources & evidence

ORD record: ord-b48129177a3a4a47b9f155feaf4f334c
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981918B2

Reaction notes

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