Allyl bromide → HCID 86714058, compound

HRID 576349Notes

Reaction equation

HRID 576349 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)=[CH:6][C:5]([CH:17]2[C@H:22]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:21]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:20]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@@H:19]([CH2:47][O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[O:18]2)=[C:4]([CH:56]=[CH2:57])[C:3]=1[OH:58].[CH2:59](Br)[CH:60]=[CH2:61].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:61]([O:58][C:3]1[C:4]([CH:56]=[CH2:57])=[C:5]([CH:17]2[C@H:22]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:21]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:20]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C@@H:19]([CH2:47][O:48][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[O:18]2)[CH:6]=[C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)[C:2]=1[Cl:1])[CH:60]=[CH2:59]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 86714059HCID 86714059, compound

Product 1

HCID 86714058HCID 86714058, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of compound 82 (320 mg, 0.4 mmol) and allyl bromide (0.05 mL, 0.6 mmol) and K2CO3 (110 mg, 0.8 mmol) in acetone (2.0 mL) was stirred for 18 hours under reflux. The mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 83 (130 mg, 37%) as colorless oil.

Workup

  1. temperatureunder reflux
  2. customThe mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b04e2e3f42db4813a289774ab4e7e04b
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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