Acetic Acid → HCID 57558470, compound

HRID 1723968Notes

Reaction equation

HRID 1723968 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:29])[C:20]=2[CH2:21][O:22]C2CCCCO2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.O>O1CCCC1>[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:29])[C:20]=2[CH2:21][OH:22])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 962Water2×HCID 57558438HCID 57558438, compound

Product 1

HCID 57558470HCID 57558470, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

2-(4-Tertbutylbenzyl)thio-3-((2-tetrahydropyranyloxy)methyl) chromen-4-one (5.5 g, 12.55 mmol) is dissolved in tetrahydrofuran in a 50 mL round bottom flask. Acetic acid and water are then added such that the ratio of THF:Acetic acid:Water is 4:2:1 (28 mL). The flask is warmed to 45° C. and the mixture stirred for 3 hours. After cooling the flask the contents are poured into a separatory funnel and the aqueous layer extracted with ethyl acetate. The organic layer is then washed with water 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 acetate:hexanes) to give the above-mentioned product.

Workup

  1. temperatureAfter cooling the flask the contents
  2. additionare poured into a separatory funnel
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. washThe organic layer is then washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo
  8. customthe residue obtained
  9. customis purified by silica gel flash chromatography (ethyl acetate:hexanes)
  10. customto give the above-mentioned product

Sources & evidence

ORD record
ord-5a1bc10e9a6b4198b1ce6dfc2cc1c2b3
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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