Acetic Acid → HCID 3529815, compound

HRID 1675919Notes

Reaction equation

HRID 1675919 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.[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)([O-:25])=[O:24].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:30][C:29]2[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)[CH2:18]1)[CH2:5][CH2:6]3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 5870EstroneHCID 14797Potassium Hydroxide

Product 1

HCID 3529815HCID 3529815, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (2.0 9) was added to a suspension of estrone (1.352 g, 5.0 mmol) and 4-nitro-benzaldehyde (755 mg, 5.0 mmol) in ethanol (80 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 (colour changes to orange). The product precipitated and was filtered off, washed with water (50 mL), ethanol (50 mL) and diethyl ether (50 mL) and dried under high vacuum. Yield: 1.682 g (83%) yellow solid. 1H-NMR (DMSO-d6, 400 MHz), δ: 0.93 (s, 3H, —CH3), 1.30-1.68 (m, 5H), 1.86-1.92 (m, 1H), 1.96-2.04 (m, 1H), 2.16-2.24 (m, 1H), 2.32-2.39 (m, 1H), 2.62-2.82 (m, 2H), 2.88-2.96 (m 1H), 6.46 (d, J=2.3 Hz, 1H), 6.52 (dd, J=8.6, 2.3 Hz, 1H), 7.06 (d, J=8.6 Hz, 1H), 7.42 (s, 1H), 7.92 (d, J=8.6 Hz, 2H), 8.27 (d, J=8.6 Hz, 2H), 9.04 (s, 1H, —OH). LRMS (FAB+): 404.1 (100, [M+H]+).

Workup

  1. customThe product precipitated
  2. filtrationwas filtered off
  3. washwashed with water (50 mL), ethanol (50 mL) and diethyl ether (50 mL)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-aa50b2edfce8403d89cb78b90fbd5ce3
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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