Butyl bromide → HCID 57247553, compound

HRID 2288083Notes

Reaction equation

HRID 2288083 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)[CH2:59][CH2:60][CH3:61]>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][CH2:59][CH2:60][CH3:61])[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 8002Butyl bromideHCID 24758Sodium hydrideHCID 56626166HCID 56626166, compound

Product 1

HCID 57247553HCID 57247553, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32 mg of compound (6) was dissolved in 0.4 ml of dry dimethylformamide under a nitrogen atmosphere and mixed with about 5 mg of sodium hydride under cooling with ice. After 15 minutes, 25.6 μl of butyl bromide was added, and the reaction solution was stirred for 50 minutes. The reaction solution was allowed to react at room temperature further for 13 hours under stirring. Then, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×22 cm) and eluted with n-hexane-ethyl acetate (4:1) to give 26 mg of compound (36) as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. customto react at room temperature further for 13 hours
  3. stirringunder stirring
  4. additionThen, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×22 cm)
  5. washeluted with n-hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-0b6187a6fe294f4a9753fe92b0e8892c
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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