Sodium Chloride → HCID 22456877, compound

HRID 2186524Notes

Reaction equation

HRID 2186524 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([I:21])[C:16]=1[O:17][CH2:18][CH2:19][CH3:20])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[C:25]([O:29][CH2:30][CH3:31])(=[O:28])[CH:26]=[CH2:27].[Na+].[Cl-]>CN(C=O)C.C(OCC)(=O)C>[CH2:30]([O:29][C:25](=[O:28])[CH2:26][CH2:27][C:12]([C:11]1[CH:14]=[C:15]([I:21])[C:16]([O:17][CH2:18][CH2:19][CH3:20])=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)=[O:13])[CH3:31]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8821Ethyl AcrylateHCID 8929Sodium CyanideHCID 22456881HCID 22456881, compound

Product 1

HCID 22456877HCID 22456877, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-benzyloxy-4-propoxy-5-iodo benzaldehyde (25.5 g, 0.064 mol) in DMF (155 ml) was added sodium cyanide (0.78 g, 0.016 mol) and stirred at room temperature for 45 min under nitrogen atmosphere. Ethyl acrylate (5.21 g, 0.057 mol) in DMF (30 ml) was added slowly and stirred at room temperature for 30-40 mints. Ethyl acetate (185 ml) and 15% NaCl solution were added to the reaction mixture and the two layers were separated. The aqueous phase was extracted with ethyl acetate (250 ml). The combined organic extracts were washed with saturated aqueous NaHCO3 (125 ml) followed by 5% aqueous NaCl (180 ml). The ethyl acetate layer was dried Na2SO4), filtered and concentrated. The crude product was purified on silica gel column using ethyl acetate:light petroleum (1:12) as eluent to give ethyl-4-(3-benzyloxy 4-propoxy-5-iodophenyl)-4-oxo-1-butanoate as a syrup (23.80 g, 74%). TLC: Ethyl acetate:light petroleum (1:9), Rf=0.4; 1H NMR (CDCl3, 200 MHz): δ 1.05 (t, J=7.4 Hz, 3H), 1.3 (t, J=6.97 Hz, 3H) 1.78 (m, 2H), 2.7 (t, J=6.5 Hz, 2H), 3.1 (t, J=6.5 Hz, 2H), 4.06 (t, J=5.6 Hz, 2H), 4.18(q, J=7.1 Hz, 2H), 5.12 (s, 2H), 7.33-7.43 (m, 5H), 7.58 (d, J=1.62 Hz, 1H), 7.97 (d, J=1.62 Hz, 1H); IR (neat): 2970, 2930, 1735, 1690, 1585, 1550 cm−1

Workup

  1. stirringstirred at room temperature for 30-40 mints
  2. customthe two layers were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (250 ml)
  4. washThe combined organic extracts were washed with saturated aqueous NaHCO3 (125 ml)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on silica gel column

Sources & evidence

ORD record
ord-cdd0efdcaa01421a96a53a04b693fe7b
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

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