Allyl bromide → HCID 131725777, compound

HRID 1827306Notes

Reaction equation

HRID 1827306 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][O:6][C:7]1[CH:44]=[CH:43][C:10]([C:11]([O:26][CH2:27][C@@:28]23[CH2:41][O:40][C@@H:30]([C@H:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[OH:39])[O:32]2)[C@@H:29]3[OH:42])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C@@H:31]1[O:32][C@:28]2([CH2:27][O:26][C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:10]3[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:44][CH:43]=3)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C@@H:29]([OH:42])[C@H:30]1[O:40][CH2:41]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 131725778HCID 131725778, compound

Product 1

HCID 131725777HCID 131725777, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Allyl bromide (0.017 ml, 0.20 mmol) was added to an anhydrous acetone (16 ml) solution of the compound (28) (96 mg, 0.18 mmol), whereafter potassium carbonate (27 mg, 0.20 mmol) was added, and the mixture was stirred for 40 hours at room temperature. After the solvent was distilled off under reduced pressure, the residue was extracted with ethyl acetate 3 times. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain a colorless oily substance (29) (90 mg, 87%).

Workup

  1. additionwas added
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate 3 times
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0774c06951be4edb89942aad50033f19
Source dataset
uspto-grants-2006_05
Patent number
US07053199B2

Reaction notes

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