Hydrochloric Acid → HCID 85836159, compound

HRID 966870Notes

Reaction equation

HRID 966870 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[CH2:5]([OH:7])[CH3:6].C(O[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=O)C.[Br-].C([P+](CCCC)(CCCC)CC1OCCO1)CCC.Cl>CN(C=O)C>[C:2]([O:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([N:19]([C:16]2[CH:15]=[CH:14][C:13]([CH:12]=[CH:6][CH:5]=[O:7])=[CH:18][CH:17]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:21][CH:22]=1)(=[O:3])[CH3:1]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2723922Sodium ethoxideHCID 22292430Tributyl(1,3-dioxolan-2-ylmethyl)phosphonium BromideHCID 22292448HCID 22292448, compound

Product 1

HCID 85836159HCID 85836159, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of NaOEt in ethyl alcohol (1M, 0.03 mol, 30 mL) was added dropwise to a solution of 4-[4′-Formyl-N.N-diphenylamino]benzyl acetate (3.45 g, 0.01 mol) and tributyl(1,3-dioxolan-2-ylmethyl)phosphonium bromide (0.54 M in DMF, 0.03 mol, 30 mL) in DMF (20 mL). The temperature of the mixture was raised to 90° C. and stirred overnight. After cooling the solution to room temperature, aqueous HCl (3M, 30 mL) was added dropwise, the mixture stirred for 1 hour, poured into ice (75 g), and the product extracted with ethyl ether (3×30 mL). The combined extracts were washed with saturated Na2CO3 solution and brine, dried over MgSO4 and the solvent evaporated. The product was purified by dissolving in warm ethanol, filtering, and evaporating the solvent to yield the desired product (2.80 g, 81%). m.p. 112-115° C.; 1H NMR δ: 2.0 (s, 3H, CH3), 4.68 (s, 2H, CH2O),6.53-6.64 (dd, 2H, vinyl), 7.0-7.4 (m, 13H, phenyl), 9.62-9.65 (d, 1H, CHO). Analysis: Calculated for C24H21NO3: C, 77.49%; H, 5.82%; N, 3.76%. Found: C, 77.38%; H, 5.54%; N, 3.62%.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. stirringthe mixture stirred for 1 hour
  3. extractionthe product extracted with ethyl ether (3×30 mL)
  4. washThe combined extracts were washed with saturated Na2CO3 solution and brine
  5. dry with materialdried over MgSO4
  6. customthe solvent evaporated
  7. customThe product was purified
  8. dissolutionby dissolving in warm ethanol
  9. filtrationfiltering
  10. customevaporating the solvent

Sources & evidence

ORD record
ord-606032f68f2b45619bcbada9faa29da5
Source dataset
uspto-grants-2005_10
Patent number
US06953570B2

Reaction notes

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