Pyridine → HCID 12561234, compound

HRID 240828Notes

Reaction equation

HRID 240828 reaction equation
[CH2:1]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([O-])(O)=[O:19].[Na+].C1C(=O)N(Br)C(=O)C1.N1C=CC=CC=1>CC(C)=O.O>[O:19]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])/[CH:17]=[CH:16]/[CH:15]=[O:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 125641122-Dodecylfuran

Product 1

HCID 12561234HCID 12561234, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent2×

Conditions

Temperature
-20 °C

Procedure

A mixture of 2-dodecylfuran (1.00 g, 4.24 mmol) and NaHCO3 (712 mg, 8.48 mmol) in acetone/H2O (10:1, 2 ml) was treated at −20° C. with NBS (905 mg, 5.11 mmol) dissolved in acetone/H2O (10 ml). After the mixture had been stirred for 1 h at −20° C., it was treated with pyridine (0.69 ml, 8.48 mmol). Thereafter, the reaction mixture came to RT, and stirring was continued for 2 h. The solution was washed with 1 N HCl, followed by extraction with ethyl acetate (2×50 ml). The organic phase was dried over NaSO4 and concentrated in order to obtain the crude product. The latter was purified by column chromatography (DCM) to give the product as a pale yellow oil (642 mg, 2.55 mmol, 60%). 1H NMR (300 MHz, CDCl3) δ 1H ppm: 0.88 (t, 3H, J=6.7 Hz, H-16), 1.19-1.36 (m, 18H), 1.59-1.71 (m, H-5), 2.69 (t, 2H, J=7.8 Hz, H-5), 6.73-6.92 (m, 2H, H-2.3), 9.78 (d, CHO, J=7.0 Hz, H-1); 13C NMR (75.5 MHz, CDCl3) δ 13C ppm: 14.2 (C-16), 22.8, 23.7, 29.2, 29.3, 29.4, 29.5, 29.5, 29.6, 29.7, 32.0, 41.3 (C-5), 137.2 (C-2), 144.8 (C-3), 193.2 (C-1), 199.9 (C-4); (−)-ESI-CID-MS: 251 [M−H]−; ESI-FT-ICR-MS: m/z 251.20137 (calculated for C16H27O2−, m/z 251.20165).

Workup

  1. customcame to RT
  2. stirringstirring
  3. waitwas continued for 2 h
  4. washThe solution was washed with 1 N HCl
  5. extractionfollowed by extraction with ethyl acetate (2×50 ml)
  6. dry with materialThe organic phase was dried over NaSO4
  7. concentrationconcentrated in order
  8. customto obtain the crude product
  9. customThe latter was purified by column chromatography (DCM)

Sources & evidence

ORD record
ord-e6b6e7bf705349ab90106f7c0d591f14
Source dataset
uspto-grants-2014_02
Patent number
US08648115B2

Reaction notes

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