Allyl bromide → HCID 86714093, compound

HRID 576433Notes

Reaction equation

HRID 576433 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:20]2)[C:3]=1[OH:58].C([O-])([O-])=O.[K+].[K+].[CH2:65](Br)[CH:66]=[CH2:67]>CC(C)=O.C([O-])(O)=O.[Na+]>[CH2:67]([O:58][C:3]1[C:2]([Br:1])=[C:7]([Cl:8])[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=[CH:5][C:4]=1[CH:19]1[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:22]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[O:20]1)[CH:66]=[CH2:65]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 86714094HCID 86714094, compound

Product 1

HCID 86714093HCID 86714093, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromo-3-chloro-4-(4-ethoxybenzyl)-6-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenol (500 mg, 0.579 mmole) in acetone (15 mL) were added K2CO3 (120 mg, 0.869 mmole) and allyl bromide (75 μL, 0.869 mmole) continuously. The resulting solution was stirred at 60° C. overnight, diluted with a saturated NaHCO3 and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound (325 mg, 62%) as a colorless gum.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record
ord-a5ff867272a94f3cb18d8e3884171ad1
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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