HCID 69542107, compound → HCID 21880349, compound

HRID 724350Notes

Reaction equation

HRID 724350 reaction equation
[CH:1]([C:4](=[CH2:19])[C:5]([C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[C:16](C)[CH:15]=[CH:14][CH:13]=2)[CH:11]=1)=[O:6])([CH3:3])[CH3:2].[CH3:20]S(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[CH3:20][C:9]1[S:8][C:7]2[C:5](=[O:6])[CH:4]([CH:1]([CH3:2])[CH3:3])[CH2:19][C:11]=2[C:10]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 69542107HCID 69542107, compoundHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 21880349HCID 21880349, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(isopropyl)-1-(5-methyl-4-phenyl(2-thienyl))prop-2-en-1-one (98 g crude product) and Eaton's reagent (200 mL) was heated to 90° C. with stirring. After 10 minutes, the reaction mixture was poured slowly into water (500 mL). The product was extracted with dichloromethane, washed with a saturated aqueous solution of NaHCO3, and dried (MgSO4). Rotoevaporation of solvent gave 98 g of crude product (˜70% product by GC/MS). A portion of the product was further refined by chromatography on silica. 1H-NMR δ (CDCl3): 7.15–7.4 (m, 5H), 2.7 (m, 2H), 2.5 (m, 1H), 2.38 (s, 3H), 2.3 (m, 1H), 0.9 (d, 3H). EIMS: m/z (%) 270 (M+, 10), 255 (4), 228 (100), 213 (5), 195 (5), 184 (10), 165 (7), 152 (6).

Workup

  1. extractionThe product was extracted with dichloromethane
  2. washwashed with a saturated aqueous solution of NaHCO3
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e857d744d2c34336a934babafa7f9ea2
Source dataset
uspto-grants-2006_11
Patent number
US07141637B2

Reaction notes

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