Acetic Acid → HCID 67349760, compound

HRID 1675918Notes

Reaction equation

HRID 1675918 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.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH:28]=O.C(O)(=O)C>C(O)C.O>[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:28][C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[CH2:18]1)[CH2:5][CH2:6]3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5870EstroneHCID 73642-ThiophenecarboxaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 67349760HCID 67349760, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (2.0 g) was added to a suspension of estrone (1.352 g, 5.0 mmol) and thiophene-2-carboxaldehyde (561 mg, 5.0 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, the product started to precipitate after a few minutes and was filtered off, washed with water (20 mL), ethanol (10 mL) and diethyl ether (10 mL) and dried under high vacuum. Yield: 1.614 g (89%) yellow solid. 1H-NMR (CDCl3, 400 MHz) δ: 0.98 (s, 3H, —CH3), 1.44-1.78 (m, 5H), 2.02-2.14 (m, 2H), 2.26-2.46 (m, 3H), 2.84-3.02 (m, 3H), 4.98 (s, 1H, —OH), 6.62 (d, J=2.7 Hz, 1H), 6.67 (dd, J=8.6, 2.7 Hz, 1H), 7.14 (dd, J=5.1, 3.5 Hz, 1H), 7.17 (d, J=8.6 Hz, 1H), 7.35 (d, J=3.5 Hz, 1H), 7.53 (d, J=5.1 Hz, 1H), 7.67 (s, 1H). LRMS (FAB+): 365.2 (100, [M+H]+).

Workup

  1. customto precipitate after a few minutes
  2. filtrationwas filtered off
  3. washwashed with water (20 mL), ethanol (10 mL) and diethyl ether (10 mL)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-9c31d14905d5456fb497798ee8f8fe46
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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