1-Chloropentane → HCID 15459993, compound

HRID 2288086Notes

Reaction equation

HRID 2288086 reaction equation
C1(C([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](C(C)(C)C)(C)C)[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])C2C=CC=CC=2)C=CC=CC=1.[H-].[Na+].Cl[CH2:59][CH2:60][CH2:61][CH2:62]C>CN(C)C=O>[CH2:59]([O:43][CH:42]1[CH:37]2[CH:38]3[O:39][C:35]([O:34][CH2:33][C:21]45[CH:20]6[CH2:29][C:28]([CH:30]=[O:31])([C:17]4([C:15]([OH:14])=[O:16])[C:18]([CH:53]([CH3:55])[CH3:54])=[CH:19]6)[CH:27]4[CH:23]([CH:24]([CH3:32])[CH2:25][CH2:26]4)[CH2:22]5)([CH:44]([OH:45])[CH:41]1[O:40]3)[O:36]2)[CH2:60][CH2:61][CH3:62]

Participants

5

Reactant 3

HCID 109771-ChloropentaneHCID 24758Sodium hydrideHCID 56626166HCID 56626166, compound

Product 1

HCID 15459993HCID 15459993, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of compound (6) was dissolved in 0.5 ml of dry dimethylformamide under a nitrogen atmosphere and mixed with about 5 mg of sodium hydride under cooling with ice. After 30 minutes, 78.7 μl of 1-chloropentane was added, and the reaction solution was stirred at room temperature for 4 hours. Then, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm) and eluted with n-hexane-ethyl acetate (5:1). The fraction containing the desired product was concentrated to dryness to give 22.0 mg of compound (38).

Workup

  1. temperatureunder cooling with ice
  2. additionThen, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm)
  3. washeluted with n-hexane-ethyl acetate (5:1)
  4. additionThe fraction containing the desired product
  5. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-503f7c7c2ff5479ea0288fbdf46b98b9
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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