Methanol → HCID 18385696, compound

HRID 2298300Notes

Reaction equation

HRID 2298300 reaction equation
[CH2:1]([C:3]([OH:18])([CH2:16][CH3:17])[C:4]#[C:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=1)=O)[CH3:2].C(NCC)C.C[OH:25]>>[CH2:16]([C:3]1([CH2:1][CH3:2])[C:4](=[O:25])[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([S:14][CH3:15])=[CH:12][CH:13]=2)[O:18]1)[CH3:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 8021DiethylamineHCID 18386051HCID 18386051, compound

Product 1

HCID 18385696HCID 18385696, compound

Procedure

A solution 10 g of 4-ethyl-4-hydroxy-1-{4-(methylthio)phenyl}-2-hexyn-1-one in 300 ml methanol was stirred in the presence of 4 ml diethylamine at room temperature for 12 hours. Then the solvent was removed in vacuo and the resulting residue was extracted with dilute aqueous HCl and dichloromethane (50 ml×3). The organic layer was washed with brine and then concentrated under reduced pressure to yield 5.6 g of 2,2-diethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone. The crude product was used for the next step without further purification. NMR: δ0.85 (t, J=7.5 Hz, 6H), 1.88 (q, J=7.5 Hz, 4H), 2.54 (s, 3H), 5.96 (s, 1H), 7.31 (d, J=9.0 Hz, 2H), 7.75 (d, J=9.0 Hz, 2H). IR (cm−1): 2971, 1690, 1597, 1487, 1408, 1364, 1162, 1095.

Workup

  1. customThen the solvent was removed in vacuo
  2. extractionthe resulting residue was extracted with dilute aqueous HCl and dichloromethane (50 ml×3)
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89d4fb5310944ea8ba051879be8d2a6b
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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