Acetic Acid → HCID 67350119, compound

HRID 1675917Notes

Reaction equation

HRID 1675917 reaction equation
[OH-].[K+].[CH3:3][C@@:4]12[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C@H:16]1[C@@H:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:22])=[CH:12][C:13]=3[CH2:14][CH2:15]1)[CH2:6][CH2:5]2.[CH:23](=O)[C:24]1[O:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)C>C(O)C.O>[O:28]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH:23]=[C:19]1[C:20](=[O:21])[C:4]2([CH3:3])[CH:17]([CH:16]3[CH:7]([CH2:6][CH2:5]2)[C:8]2[CH:9]=[CH:10][C:11]([OH:22])=[CH:12][C:13]=2[CH2:14][CH2:15]3)[CH2:18]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5870EstroneHCID 7362FurfuralHCID 14797Potassium Hydroxide

Product 1

HCID 67350119HCID 67350119, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (2.0 g) was added to a suspension of estrone (2.704 g, 10 mmol) and furfuraldehyde (2 mL, ca. 20 mmol) in ethanol (40 mL). The resulting dark brown solution was stirred for 4 hours at room temperature, then acetic acid (5 mL) and water (5 ml) were added. After a few minutes the product started to precipitate. The precipitation was completed by addition of more water (ca. 10 mL). The yellow solid was filtered off, washed with water, dissolved in chloroform and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was crystallised from ethyl acetate/hexane. Yield: 3.24 g (93%) light yellow crystals. 1H-NMR (CDCl3, 400 MHz) δ: 0.97 (s, 3H, —CH3), 1.42-1.76 (m, 5H), 2.00-2.20 (m, 2H), 2.22-2.35 (m, 1H), 2.36-2.51 (m, 2H), 2.82-3.00 (m, 2H), 3.14 (ddd, J=15.2, 6.6, 1.6 Hz, 1H), 5.08 (s, 1H, —OH),6.52 (dd, J=3.1, 1.6 Hz, 1H),6.62 (d, J=2.7 Hz, 1H),6.64-6.70 (m, 2H),7.16 (d, J=8.2 Hz, 1H), 7.22-7.27 (m, 1H), 7.57 (d, J=1.6 Hz, 1H). LRMS (FAB+): 349.2 (100, [M+H]+).

Workup

  1. waitAfter a few minutes the product started
  2. customto precipitate
  3. customThe precipitation
  4. additionwas completed by addition of more water (ca. 10 mL)
  5. filtrationThe yellow solid was filtered off
  6. washwashed with water
  7. dissolutiondissolved in chloroform
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c3837fe26d7d49e299a493c83a65046f
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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