Water → HCID 15589953, compound

HRID 463038Notes

Reaction equation

HRID 463038 reaction equation
[C:1]([C:6]1[S:10][C:9]([CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[OH2:15]>O1CCOCC1>[C:1]([C:6]1[S:10][C:9](/[CH:11]=[C:12](\[CH3:13])/[CH:14]=[O:15])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 20282864HCID 20282864, compound

Product 1

HCID 15589953HCID 15589953, compoundYield 176.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.8 g (17.2 mmol) of 1-(5-carbethoxythien-2-yl)-2-methyl-1-propene and 5.0 g (45 mmol) of SeO2 in 60 mL of dioxane and 0.8 mL (44 mmol) of H2O was degassed three times under argon and heated under reflux for 45 min. Cooling, filtration over Celite, and concentration gave 6.8 g of a light-brown solid, which was diluted with 50 mL of Et2O and filtered. The filtrate was concentrated and passed over a column of 150 g of silica gel (15% EtOAc/hexane) to give 2.35 g (60% yield) of the aldehyde as a pale yellow solid, a portion of which was recrystallized from EtOAc/hexane to give white needles, mp 98° C.: IR (mull) 1720, 1680, 1620, 1380, 1290, 1250, 1180, 1160, 1100, 1020, 890, 850, 815, 750 cm-1 ; 1H NMR (CDCl3) δ1.42 (t, J=7 Hz, 3, CH2CH3), 2.17 (s, 3, C=CCH3), 4.47 (q, J=7 Hz, 2, CH2CH3), 7.40 (d, J=4 Hz, 1, 3' C=CH), 7.43 (s, 1, C=CH), 7.83 (d, J=4 Hz, 1, 4' C=CH), 9.63 (s, 1, CHO); MS calcd for C11H12O3S 224.0507, found 224.0519.

Workup

  1. customwas degassed three times under argon
  2. temperatureheated
  3. temperatureunder reflux for 45 min
  4. temperatureCooling
  5. filtrationfiltration
  6. concentrationover Celite, and concentration

Sources & evidence

ORD record
ord-627de1ba516645ac884d44369947d421
Source dataset
uspto-grants-1985_05
Patent number
US04518609

Reaction notes

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