Allyl bromide → HCID 69589206, compound

HRID 1796858Notes

Reaction equation

HRID 1796858 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:32](Br)[CH:33]=[CH2:34]>C1COCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[C@@H:15]([CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH2:34][CH:33]=[CH2:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 69589125HCID 69589125, compound

Product 1

HCID 69589206HCID 69589206, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred −78° C. solution of Example 8B (15.65 g, 54.2 mmol) in THF (160 mL) was added sodium bis(trimethylsilyl)amide (55 mL, 1M in THF). The reaction mixture was stirred for 45 minutes and allyl bromide (5.3 mL, 60.9 mmol) was added. The reaction mixture was stirred for 90 minutes, warmed to 0° C., and stirred an additional 90 minutes. The reaction was quenched with saturated ammonium chloride, concentrated, and partitioned between water and ethyl acetate. The organic layer was washed sequentially with water, 1M sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 330 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 90 minutes
  2. stirringstirred an additional 90 minutes
  3. customThe reaction was quenched with saturated ammonium chloride
  4. concentrationconcentrated
  5. custompartitioned between water and ethyl acetate
  6. washThe organic layer was washed sequentially with water, 1M sodium bicarbonate, water, and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d90757e3caf941c5838173bb866bfbc1
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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