Dimethylformamide → HCID 86747527, compound

HRID 2209447Notes

Reaction equation

HRID 2209447 reaction equation
[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH2:11](Br)[CH:12]=[CH2:13].[I-].[CH3:16][N:17]([CH:19]=[O:20])[CH3:18]>CCOCC>[C:19]([N:17]1[CH2:18][CH2:13][CH:12]([CH2:11][CH2:12][CH:13]=[C:16]([N:17]2[CH2:18][CH2:19][NH:17][C:19]2=[O:20])[CH3:18])[CH2:11][CH2:16]1)([O:20][C:12]([CH3:13])([CH3:16])[CH3:11])=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 30165Iodide IonHCID 178418261HCID 178418261, compound2×

Product 1

HCID 86747527HCID 86747527, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 13 (1.5 g, 17 mmol) in DMF (75 mL) at ambient temperature was added LiN(TMS)2 (1M in hexanes, 17 mL) to effect a precipitate. Allyl bromide (1.6 mL, 19 mmol) was then added to the reaction mixture. After 15 min the homogeneous mixture was treated again with LiN(TMS)2 (14 mL) followed by the iodide 10 (5.9 g, 17 mmol) after 5 min. The reaction was stirred for 20 hr then diluted with ether. The ether portion was washed with water (2×), 5% KHSO4 and brine, dried (Mg SO4), and concentrated. Flash chromatography (40% ethyl acetate/hexanes) gave 14 (0.8 g, 15%) as a colorless oil.

Workup

  1. washThe ether portion was washed with water (2×), 5% KHSO4 and brine
  2. dry with materialdried (Mg SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c65c5add0063416f868ca4b2ce090ae3
Source dataset
uspto-grants-1995_10
Patent number
US05455243

Reaction notes

Loading…