HCID 67609415, compound → HCID 67609367, compound

HRID 1847120Notes

Reaction equation

HRID 1847120 reaction equation
[OH:1][C@@H:2]1[CH2:24][C@@H:6]2[C:7](=[O:23])[O:8][C:9]3[C@@H:10]4[CH2:17][CH2:16][C@H:15]([C@H:18]([CH3:21])[CH2:19][OH:20])[C@@:11]4([CH3:22])[CH2:12][CH2:13][C:14]=3[C@@:5]2([CH3:25])[CH2:4][CH2:3]1>C(Br)C=C.[Ag]=O>[CH3:7][O:8][CH2:9][O:1][C@@H:2]1[CH2:24][C@@H:6]2[C:7](=[O:23])[O:8][C:9]3[C@@H:10]4[CH2:17][CH2:16][C@H:15]([C@H:18]([CH3:21])[CH2:19][O:20][CH2:6][C:5]([CH3:14])=[CH2:4])[C@@:11]4([CH3:22])[CH2:12][CH2:13][C:14]=3[C@@:5]2([CH3:25])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 67609415HCID 67609415, compound

Product 1

HCID 67609367HCID 67609367, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 7841Allyl bromideSolvent

Procedure

Compound 95 (7.6 mg, 0.019 mmol) obtained in Example 67 was dissolved in allylbromide (0.5 mL), and silver oxide (986 mg, 4.25 mmol) was added thereto, followed by stirring under light shading at room temperature for 12 hours. Silver oxide was separated by filtration, the filtrate was concentrated, and then the residue was purified by silica gel column chromatography (33% ethyl acetate/n-hexane) to obtain the title compound (4.2 mg, 48%).

Workup

  1. customSilver oxide was separated by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography (33% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-45e737fb8555483f8da8541e4ded60a3
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

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