2-Bromopropane → HCID 56634327, compound

HRID 2288080Notes

Reaction equation

HRID 2288080 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[CH:59]([CH3:61])[CH3:60]>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][CH:59]([CH3:61])[CH3:60])[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 63582-Bromopropane2×HCID 24758Sodium hydride2×HCID 56626166HCID 56626166, compound

Product 1

HCID 56634327HCID 56634327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of compound (6) was dissolved in 1.0 ml of dry dimethylformamide under a nitrogen atmosphere and mixed with about 3 mg of sodium hydride under cooling with ice. After 30 minutes, 12.2 μl of 2-bromopropane was added, and the reaction solution was stirred at room temperature. The reaction solution was allowed to react for 63 hours, while about 3 mg of sodium hydride and 12.2 μl of 2-bromopropane were added after 40 hours and further after 46 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 (2:1). The fraction containing the desired product was concentrated to dryness to give 13.6 mg of compound (33).

Workup

  1. temperatureunder cooling with ice
  2. additionwere added after 40 hours and further after 46 hours
  3. additionThen, the reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm)
  4. washeluted with n-hexane-ethyl acetate (2:1)
  5. additionThe fraction containing the desired product
  6. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-dd174f1eee4e408aa585647088a5ceea
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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