HCID 67609415, compound → HCID 68008633, compound

HRID 1847118Notes

Reaction equation

HRID 1847118 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>[CH2:24]([O:20][CH2:19][C@H:18]([C@@H:15]1[C@@:11]2([CH3:22])[CH2:12][CH2:13][C:14]3[C@@:5]4([CH3:25])[CH2:4][CH2:3][C@H:2]([O:1][CH2:7][O:8][CH3:9])[CH2:24][C@@H:6]4[C:7](=[O:23])[O:8][C:9]=3[C@@H:10]2[CH2:17][CH2:16]1)[CH3:21])[CH:2]=[CH2:3]

Participants

4

Reactant 1

HCID 67609415HCID 67609415, compound

Product 1

HCID 68008633HCID 68008633, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 7841Allyl bromideSolvent

Procedure

Compound 95 (16.7 mg, 0.0425 mmol) obtained in Example 67 was dissolved in allylbromide (2 mL), and silver oxide (986 mg, 4.25 mmol) was added thereto, followed by stirring under light shading at room temperature for 14 hours. Silver oxide was separated by filtration, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (33% ethyl acetate/n-hexane) to obtain the title compound (3.7 mg, 21%).

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-e5ab6fc22fac41109e698a626d8eff6f
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

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