Water → HCID 57558444, compound

HRID 2382529Notes

Reaction equation

HRID 2382529 reaction equation
[CH2:1]([S:3]([C:5]1[O:6][C:7]2[C:12]([C:13](=[O:17])[C:14]=1[CH2:15][OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH3:2].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C1(C)C(S(O)(=O)=O)=CC=CC=1.O>ClCCl.C(OCC)(=O)C>[CH2:1]([S:3]([C:5]1[O:6][C:7]2[C:12]([C:13](=[O:17])[C:14]=1[CH2:15][O:16][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][O:18]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 69252-Methylbenzenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 57558465HCID 57558465, compound

Product 1

HCID 57558444HCID 57558444, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-ethylsulfinyl-3-hydroxymethyl chromen-4-one (5 g, 19.8 mmol) dissolved in dichloromethane (20 mL) in a 25 mL round bottom flask is added dihydropyran (29.7 mmol) and toluenesulfonic acid (0.99 mol). The reaction mixture is stirred for 3 hours after which it is poured into a separatory funnel and water is added. Ethyl acetate is then added and the layers are separated. The organic layer is washed with water (3×10) and brine and dried over sodium sulfate and filtered. The filtrate is concentrated in vacuo and the residue obtained is purified by silica gel flash chromatography (ethyl ether:hexanes) to yield the above product.

Workup

  1. additionis poured into a separatory funnel
  2. customthe layers are separated
  3. washThe organic layer is washed with water (3×10) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue obtained
  8. customis purified by silica gel flash chromatography (ethyl ether:hexanes)
  9. customto yield the above product

Sources & evidence

ORD record
ord-2869ce01a0d4463c8bda529f320502b1
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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