Ethyl acetate hexane → HCID 22676834, compound

HRID 1006279Notes

Reaction equation

HRID 1006279 reaction equation
[C:1]([O:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[C:15]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:16]2S(C2C=CC=CC=2)(=O)=O)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].C(OCC)(=O)C.CCCCCC>O1CCCC1>[C:1]([O:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[C:15]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[NH:16]2)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 22676749HCID 22676749, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22676834HCID 22676834, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a dry 100 mL and stir bar was charged with 4.70 g ethyl 6-(benzoyloxy)-1-(phenylsulfonyl)indole carboxylate (Example 210) and dissolved in 12.5 mL of anhydrous tetrahydrofuran then cooled to 0° C. To this rapidly stirring solution was added 35.0 mL 1.0 M tetrahydrofuran solution of potassium tert-butoxide dropwise via syringe. Upon complete addition the contents were warmed to room temperature and stirred an additional ½ hour then quenched with 10 mL of 3N HCl solution followed by addition of 30 mL of water. The reaction was extracted with 3×50 mL of ethyl acetate then dried over Na2SO4 and concentrated in vacuo. The crude material was purified via column chromatography to yield 3.28g (99.0% yield) of an off white solid. The product had a Rf of 0.42 20% ethyl acetate/hexane; 1H NMR (300 MHz, Acetone-D6); 8.80 Hz, (s, 1H), 8.02 Hz, (dd, 1H), 7.95 Hz, (dd, 1H), 7.68 Hz, (dd, 1H), 7.58 Hz, (m, 2H), 7.46 Hz, (d, 2H), 7.21 Hz, (d, 1H), 6.87 Hz, (dd, 1H), 4.31 Hz (q, 2H), 1.31 Hz (t, 3H).

Workup

  1. additionUpon complete addition the contents
  2. temperaturewere warmed to room temperature
  3. stirringstirred an additional ½ hour
  4. customthen quenched with 10 mL of 3N HCl solution
  5. additionfollowed by addition of 30 mL of water
  6. extractionThe reaction was extracted with 3×50 mL of ethyl acetate
  7. dry with materialthen dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified via column chromatography
  10. customto yield 3.28g (99.0% yield) of an off white solid

Sources & evidence

ORD record
ord-363f4294283f4df1b1585d74640e99b0
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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