Allyl bromide → HCID 70045243, compound

HRID 1198499Notes

Reaction equation

HRID 1198499 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18]N2CCCC2=O)[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1.[Li+].CC([N-:34]C(C)C)C.[CH2:38](Br)[CH:39]=[CH2:40]>C(OCC)(=O)C>[C:1]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH:40]=[C:39]([CH:25]2[CH2:26][CH2:27][NH:34][C:29]2=[O:28])[CH3:38])[CH2:15][CH2:16]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 19380930HCID 19380930, compound

Product 1

HCID 70045243HCID 70045243, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 114 (8.0 g, 24.2 mmol), and THF (180 mL) at -78° C. was added LDA (50 mL, 25 mmol, 0.5M/THF) dropwise. After 15 min. allyl bromide (2.3 mL, 26.6 mmol) was added. After 1.0 hour, the reaction mixture was allowed to warm to 0° C. over a 10 min. period. The reaction mixture was diluted with ethyl acetate and then washed with 5% KHSO4 and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 50% ethyl acetate/hexanes) gave 115.

Workup

  1. washwashed with 5% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5654d722812c4530b97f33c45b93e0aa
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

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