Estrone → HCID 67351721, compound

HRID 1675914Notes

Reaction equation

HRID 1675914 reaction equation
[OH-].[Na+].[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.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=O.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>C(O)C>[OH:22][C:11]1[CH:10]=[CH:9][C:8]2[CH:7]3[CH:16]([CH2:15][CH2:14][C:13]=2[CH:12]=1)[CH:17]1[C:4]([CH3:3])([C:20](=[O:21])[C:19](=[CH:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)[CH2:18]1)[CH2:5][CH2:6]3

Participants

6

Reactant 4

HCID 5870EstroneHCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

HCID 67351721HCID 67351721, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (1.0 g, 25 mmol) was added to a suspension of estrone (1.35 g, 5.0 mmol) and pyridine-2-carbaldehyde (595 mg, 5.0 mmol) in ethanol (40 mL) at room temperature. The resulting dark orange solution was stirred at room temperature for 4 hours. Then glacial acetic (ca. 10 mL) acid was added with stirring. The colour changed to light yellow and a light yellow solid precipitated. The solid was filtered off and washed with water (50 mL), ethanol (20 mL), diethyl ether (50 mL) and hexane (50 mL) and dried under high vacuum. Yield: 1.638 g (91%) yellow powder.

Workup

  1. stirringwith stirring
  2. customprecipitated
  3. filtrationThe solid was filtered off
  4. washwashed with water (50 mL), ethanol (20 mL), diethyl ether (50 mL) and hexane (50 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-bad455e56c3748f29d10a7576191adb1
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

Loading…