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Chemical Structure| 1018673-94-3 Chemical Structure| 1018673-94-3

Structure of 1018673-94-3

Chemical Structure| 1018673-94-3

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Product Details of [ 1018673-94-3 ]

CAS No. :1018673-94-3
Formula : C11H13NO3
M.W : 207.23
SMILES Code : O=C(OCC)/C=C/C1=NC=C(CO)C=C1
MDL No. :MFCD22378841

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Application In Synthesis of [ 1018673-94-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1018673-94-3 ]

[ 1018673-94-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 34107-46-5 ]
  • [ 4417-81-6 ]
  • [ 1018673-94-3 ]
YieldReaction ConditionsOperation in experiment
Stage 2; The product from Stage 1 (46g, 1eq) was dissolved in acetic anhydride (67OmL) and stirred at 800C for approximately 1h. Ethyl glyoxal solution (50% in toluene) (147mL, 2eq) was charged to the reaction vessel which was then heated for overnight at 1000C. An additional ammount of ethyl glyoxal solution (50% in toluene) (37mL, 0.5eq) was added at approximately 16h after reflux was initiated and heating was continued for 2h. The reaction was quenched with water (10OmL), stirred at ~50C for 40 min then concentrated in vacuo. The residue was basified to pH 9-10 with 1 N NaOH and then solid NaOH. After extraction twice with EtOAc, the combined organics were washed with 0.25N NaOH then concentrated to dryness. The crude residue was stirred in a mixture of ethanol (50OmL) and cone. HCI (5OmL) for overnight at 40C. On completion of deacetylation the reaction mixture was concentrated to dryness, separated between EtOAc and K2CO3(aq)and the aqueous phase extracted with EtOAc. The combined organics were washed with K2CO3(aq), dried (MgSO4), then concentrated to dryness in vacuo. Purification by dry-flash chromatography (3:2-1 :4 heptanes:EtOAc eluant) afforded the desired product (21.9g). 1H NMR (CDCI3): 8.64 (1 H,s), 7.76-7.79 (1 H,m), 7.74 (1 H,d), 7.44 (1 H,d), 6.92 (1 H,d), 4.79 (2H,d), 4.29 (2H,q) and 1.36 (3H,t).
  • 2
  • [ 34107-46-5 ]
  • [ 924-44-7 ]
  • [ 1018673-94-3 ]
YieldReaction ConditionsOperation in experiment
Ethyl (2£)-3-f5-(hvdroxymethyl)pyridin-2-yl1prop-2-enoate(6-Methylpyridin-3-yl)methanol (75 g, 0.61 mol) and acetic anhydride (380 mL) were heated to 80 C for 1 h 20 min. 50% Ethyl glyoxal in toluene (165 mL, 0.83 mol) was added and the reaction heated to 100C for 3 h when additional 50% ethyl glyoxal (55 mL, 0.28 mmol) was added. After 2 h, EtOH (250 mL) was added and the reaction heated at reflux for 1.5 h and then concentrated to dryness. The residue was dissolved in ethanol (400mL), concentrated hydrochloric acid (40mL) charged then heated at reflux for 3h, until no further acetylated product was seen. On cooling the reaction was concentrated in vacuo to afford the crude product. Diethyl ether was charged to the concentrate, slurried, then decanted from the brown oily residue. 2N Potassium carbonate solution (400mL) and ethyl acetate (400mL) were charged to the residue then separated. The aqueous phase extracted twice with ethyl acetate (400mL). The combined organic phases were washed with brine (400mL), dried (Na2S04) and concentrated to dryness. Purification by silica chromatography (1 :1 ethyl acetate/ n- heptanes eluant) afforded the desired product (38.6g). 1H NMR (CDCI3): 8.62 (1 H, d, J=1 .8). 7.76 (1 H, dd, J=7.8, 2.1 ), 7.69 (1 H, d, J=15.9), 7.44 (1 H, d, J=7.8), 6.90 (1 H, d, J=15.6), 4.78 (2H, s), 4.26 (2H, q, J=7.2), 1 .35 (3H, t, J=7.2).
 

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