Pyridine → HCID 71730813, compound

HRID 1430397Notes

Reaction equation

HRID 1430397 reaction equation
[CH:1]1[C:6]2[C:7]#[C:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[CH2:11][CH:12]([OH:13])[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20].N1C=CC=CC=1>C(Cl)Cl>[N+:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][C:19](=[O:20])[O:13][CH:12]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:6]=3[C:7]#[C:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[CH2:11]2)=[CH:27][CH:26]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 42614041HCID 42614041, compound

Product 1

HCID 71730813HCID 71730813, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 45 (0.22 g, 1 mmol) in CH2Cl2 (30 mL) was added 4-nitro-phenyl chloroformate (0.4 g, 2 mmol) and pyridine (0.4 ml, 5 mmol). After stirring 4 hours at ambient temperature, the reacting mixture was washed with brine (2×10 mL), and the organic layer was dried (MgSO4). The solvents were evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate, 10/1, v/v) to afford 47 (0.34 g, 89%). 1H NMR (300 MHz, CDCl3): δ 8.23-8.18 (2H, aromatics), 7.56-7.54 (2H, aromatics), 7.46-7.18 (8H, aromatics), 5.52 (1H, dd, J=3.9, 15.3 Hz, CHOH), 3.26 (1H, dd, J=3.9, 15.3 Hz, CH2), 2.97 (1H, dd, J=3.9, 15.3 Hz, CH2). 13C NMR (75 MHz, CDCl3): δ 154.5, 150.7, 149.1, 148.7, 129.0, 127.4, 127.3, 126.7, 126.5, 125.5, 125.2, 124.3, 124.0, 122.6, 122.4, 120.8, 120.6, 120.2, 112.2, 108.5, 80.6, 44.8. MALDI HRMS: m/z 408.0852 [M+Na+]. Calcd for C23H15NNaO5: 408.0848.

Workup

  1. washthe reacting mixture was washed with brine (2×10 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customThe solvents were evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate, 10/1

Sources & evidence

ORD record
ord-4215d1e0aebc4c62805a8a68a1992dcb
Source dataset
uspto-grants-2015_01
Patent number
US08940859B2

Reaction notes

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