2-Bromoethanol → HCID 86714032, compound

HRID 576316Notes

Reaction equation

HRID 576316 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)[C:3]=1[OH:57].C([O-])([O-])=O.[K+].[K+].Br[CH2:65][CH2:66][OH:67]>CC(C)=O>[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH3:17])=[CH:14][CH:15]=2)[CH:5]=[C:4]([CH:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[O:19]2)[C:3]=1[O:57][CH2:65][CH2:66][OH:67]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 86714033HCID 86714033, compound

Product 1

HCID 86714032HCID 86714032, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of the intermediate 32 (2.99 g, 3.53 mmol) and K2CO3 (0.73 g, 5.29 mmol) in acetone (35 mL) was added 2-bromoethanol (0.38 mL, 5.29 mmol) at rt. After stirring for 15 h at 50° C., the reaction mixture was cooled to rt. The precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide the crude intermediate 33, which was used without further purification (3.04 g, 3.41 mmol, 97%).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afc681eb3795411f838c090f61c2ebee
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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