5-Methylfurfural → HCID 86637695, compound

HRID 1036367Notes

Reaction equation

HRID 1036367 reaction equation
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])C=CC=CC=1.[CH3:29][C:30]1[O:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[CH3:34][C:33]1[O:36][C:30](/[CH:29]=[CH:9]/[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 120975-MethylfurfuralHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2773643(3-(Ethoxycarbonyl)propyl)triphenylphosphonium Bromide

Product 1

HCID 86637695HCID 86637695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of triphenyl-(3-ethoxycarbonylpropyl)phosphonium bromide (2.27 g, 5 mmol) and 5-methylfurfural (0.55 g, 5 mmol) in 5 mL of dry tetrahydrofuran, a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (5 mL) was added dropwise. The reaction mixture was stirred at room temperature for 2 hours and quenched with 2 N hydrochloric acid solution. The reaction mixture was extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, concentrated and chromatographed eluting with 5% ethyl acetate/hexane to yield the title product: 1H NMR (300 MHz, CDCl3) δ 6.16 (d, J=3.05 Hz, 1H), 5.97 (dd, J=3.22, 0.85 Hz, 1H), 5.42 (dt, J=11.44, 7.11 Hz, 1H)), 4.14 (q, J=7.2 Hz, 2H), 2.76 (m, 2H), 2.47 (t, J=7.46 Hz, 2H), 2.31 (s, 3H), 1.25 (t, J=7.12 Hz, 3H); MS (DCI/NH3)(M+H)+ m/z 209.

Workup

  1. customquenched with 2 N hydrochloric acid solution
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customchromatographed
  6. washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-79ff3673faed4ced9daa3210e4b45c27
Source dataset
uspto-grants-2013_10
Patent number
US08546410B2

Reaction notes

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