Dimethylformamide → HCID 86747527, compound

HRID 1198489Notes

Reaction equation

HRID 1198489 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. TLC Rf=0.46 (70% ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 5.80 (m, 1H), 5.23 (m, 2H), 4.10 (m, 2H), 3.82 (m, 2H), 3.30 (m, 6H), 2.72 (m, 2H), 1.70 (m, 3H), 1.50 (m, 2H), 1.46 (s, 9H), 1.15 (m, 2H).

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-a8dd9d535df64631ab897e117e59721f
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

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