Sodium hydride → HCID 88236383, compound

HRID 2288088Notes

Reaction equation

HRID 2288088 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+].Br[CH2:59][CH:60]=[C:61]([CH3:63])[CH3:62]>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][CH2:59][CH:60]=[C:61]([CH3:63])[CH3:62])[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 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 56626166HCID 56626166, compound

Product 1

HCID 88236383HCID 88236383, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 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, 37.4 ml of 4-bromo-2-methyl2-butene was added, and the reaction solution was stirred under cooling with ice for 50 minutes. The reaction solution was allowed to react at room temperature for another 20 minutes under stirring. Then, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.5φ×19 cm) and eluted with n-hexane-ethyl acetate (10:1) to give 34.4 mg of compound (42) as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 50 minutes
  3. customto react at room temperature for another 20 minutes
  4. stirringunder stirring
  5. additionThen, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.5φ×19 cm)
  6. washeluted with n-hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-47ba7640bad44f50aa2c453a1a9610ef
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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