Allyl bromide → HCID 22086396, compound

HRID 2227263Notes

Reaction equation

HRID 2227263 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])[CH2:15][CH2:16][CH2:17][C:18]1([CH3:23])[O:22][CH2:21][CH2:20][O:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+].[CH2:37](Br)[CH:38]=[CH2:39]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])[C@H:15]([CH2:16][CH2:17][C:18]1([CH3:23])[O:19][CH2:20][CH2:21][O:22]1)[CH2:39][CH:38]=[CH2:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 22086397HCID 22086397, compoundHCID 86588160Lithim bis(trimethylsilylamide)

Product 1

HCID 22086396HCID 22086396, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-9 (19.3 g, 57.9 mmol) in tetrahydrofuran (400 mL) at −78° C. under argon was added a solution of lithium bis(trimethylsilylamide) (75.2 mL of a 1.0 M solution in tetrahydrofuran) over 20 min. After an additional 20 min., allyl bromide (14.0 g, 116 mmol) was added in one portion. After 20 min., the reaction mixture was allowed to warm to 0° C. After 3.5 h, the reaction mixture was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography (silica gel, 25 to 35% ethyl acetate/hexanes) to give 1-10 as an oil.

Workup

  1. waitAfter 20 min.
  2. waitAfter 3.5 h
  3. washwashed with water, saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting oil was purified by flash column chromatography (silica gel, 25 to 35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1fba28c3f3874640b84cbc0200dc8e9f
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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