Water → HCID 22734272, compound

HRID 1057894Notes

Reaction equation

HRID 1057894 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:20]=[C:19]([CH:21](Br)[CH:22](Br)[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[C:11]2[CH2:12][C:13]3([O:18][C:10]=2[C:9]=1[O:31][CH3:32])[CH2:17][CH2:16][CH2:15][CH2:14]3.O>C1COCC1>[Br:7][C:8]1[CH:20]=[C:19]([C:21]#[C:22][C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)[C:11]2[CH2:12][C:13]3([O:18][C:10]=2[C:9]=1[O:31][CH3:32])[CH2:14][CH2:15][CH2:16][CH2:17]3

Participants

5

Reactant 3

HCID 962WaterHCID 22734364HCID 22734364, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22734272HCID 22734272, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (0.15 g) was added to a solution of Compound 142a (0.25 g) obtained in Step A in THF (9 ml) at 0° C., followed by stirring at room temperature for 5 hours. The reaction solution was poured into water and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1) to give Compound 142b (0.12 g, 68.2%) as pale-yellow crystals.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with a saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-76aed5c35d2a4c4a9ad791608a9fc171
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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