Water → HCID 12043730, compound
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:30]([C:32]1([C:39]2[C:48]3[O:47][CH2:46][CH2:45][O:44][C:43]=3[C:42]([O:49][CH3:50])=[CH:41][CH:40]=2)[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1)#[N:31].O>C1COCC1>[CH3:50][O:49][C:42]1[C:43]2[O:44][CH2:45][CH2:46][O:47][C:48]=2[C:39]([C:32]2([C:30]#[N:31])[CH2:37][CH2:36][C:35](=[CH:2][O:3][CH3:4])[CH2:34][CH2:33]2)=[CH:40][CH:41]=1Participants
6
Procedure
To a suspension of (methoxymethyl)triphenylphosphonium chloride (34 g, 99 mmol) in THF (320 mL) was added potassium tert-butoxide (11 g, 99 mmol). The mixture was stirred at room temperature for 15 minutes, and a solution of Compound 1 (15 g, 52 mmol) obtained in Example 1 in THF (150 mL) was added dropwise, followed by stirring at room temperature for 45 minutes. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=3/1) to give Compound 6 (14 g, 82%) as a white solid.
Workup
- stirringby stirring at room temperature for 45 minutes
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated in vacuo
- customthe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=3/1)
Sources & evidence
- ORD record
- ord-207f455a1d804e57a96c418b470d1fcb
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06376535B2
Reaction notes
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