1-Chlorohexane → HCID 56621033, compound

HRID 2288091Notes

Reaction equation

HRID 2288091 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](Cl)[CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]>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][CH2:61][CH2:62][CH3:63])[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 109921-ChlorohexaneHCID 24758Sodium hydrideHCID 56626166HCID 56626166, compound

Product 1

HCID 56621033HCID 56621033, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100.0 mg of compound (6) was dissolved in 0.8 ml of dry dimethylformamide under a nitrogen atmosphere and mixed with about 10 mg of sodium hydride under cooling with ice. After 15 minutes, 44 μl of hexyl chloride was added, and the reaction solution was stirred under cooling with ice for 2 hours. The reaction solution was allowed to react at room temperature for another 90 minutes under stirring. Then, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×21 cm) and eluted with n-hexane-ethyl acetate (4:1) to give 18.7 mg of compound (45) as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 2 hours
  3. customto react at room temperature for another 90 minutes
  4. stirringunder stirring
  5. additionThen, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×21 cm)
  6. washeluted with n-hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-48ab1523d000442798544b47efc93fa8
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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