Sodium Hydroxide → HCID 10182400, compound

HRID 850600Notes

Reaction equation

HRID 850600 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][C@@H:6]([C:26]1[CH:34]=[CH:33][C:29]2[CH2:30][CH2:31][O:32][C:28]=2[CH:27]=1)[N:7]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][NH:18][C:17]=3[N:16]=2)[C:8]1=[O:25])C.[OH-].[Na+]>CCO>[O:32]1[C:28]2[CH:27]=[C:26]([C@@H:6]([N:7]3[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][C:15]4[CH:24]=[CH:23][C:22]5[CH2:21][CH2:20][CH2:19][NH:18][C:17]=5[N:16]=4)[C:8]3=[O:25])[CH2:5][C:4]([OH:35])=[O:3])[CH:34]=[CH:33][C:29]=2[CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10863743HCID 10863743, compound

Product 1

HCID 10182400HCID 10182400, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-12 (2.9 g, 6.06 mmol) in EtOH (15 mL) was added 1N NaOH (7.2 ml,7.2 mmol). After stirring for 2 h, the solvents were evaporated and the residue chromatographed (silica gel, 25:10:1:1 followed by 15:10:1:1 ethyl acetate/EtOH/water/NH4OH) to give 2-13 as a white solid. TLC Rf=0.24 (15:10:1:1 ethyl acetate/EtOH/water/NH4OH). 1H NMR (300 MHz, CD3OD) δ 7.55 (d, J=7.3 Hz, 1H), 7.18 (d, J=7.6 Hz, 1H), 6.81 (d, J=6.1 Hz, 1H), 6.72 (s, 1H), 6.62 (d, J=7.3 Hz, 1H), 5.38 (t, J=7.9 Hz, 1H), 4.53 (t, J=8.9 Hz,2H), 3.14-3.53 (9H), 2.97 (m, 3H),2.80 (t, J=6.1 Hz, 2H), 2.67 (t, J=7.3 Hz, 2H), 1.93 (m,4H). ##STR14## Ethyl 3-fluorocinnamate (3-2)

Workup

  1. customthe solvents were evaporated
  2. customthe residue chromatographed (silica gel, 25:10:1:1 followed by 15:10:1:1 ethyl acetate/EtOH/water/NH4OH)

Sources & evidence

ORD record
ord-514f07cbcfba444eaa31cc395a55f688
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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