Ethyl Bromide → HCID 57122860, compound

HRID 2288074Notes

Reaction equation

HRID 2288074 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:44]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH:41]6[CH:42]([OH:43])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:53]([CH3:55])[CH3:54])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:58](Br)[CH3:59]>CN(C)C=O>[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:44]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH:41]6[CH:42]([O:43][CH2:58][CH3:59])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:53]([CH3:55])[CH3:54])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 56626166HCID 56626166, compound

Product 1

HCID 57122860HCID 57122860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

48.0 mg of compound (6) was dissolved in 0.4 ml of dry dimethylformamide, and about 5 mg of sodium hydride was added under cooling with ice. After 15 minutes, 19 μl of ethyl bromide was added, and the reaction solution was stirred under cooling with ice. After 50 minutes, the reaction solution was brought back to room temperature and allowed to react for another 90 minutes under stirring. Then, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×25 cm) and eluted with n-hexane-ethyl acetate (4:1) to give 36.8 mg of compound (27) as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. waitAfter 50 minutes
  4. customwas brought back to room temperature
  5. customto react for another 90 minutes
  6. stirringunder stirring
  7. additionThen, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×25 cm)
  8. washeluted with n-hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-be4b9cd5cada4d4d907fc4ae592854ec
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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