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Acetic Acid → HCID 3620128, compound

HRID 1675920
Notes
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Reaction equation

HRID 1675920 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.[C:23]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)#[N: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:29][C:28]2[CH:31]=[CH:32][C:25]([C:23]#[N:24])=[CH:26][CH:27]=2)[CH2:18]1)[CH2:5][CH2:6]3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5870EstroneHCID 14797Potassium HydroxideHCID 660424-Cyanobenzaldehyde

Product 1

HCID 3620128HCID 3620128, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962
Water
Solvent

Procedure

Potassium hydroxide (2.0 g) was added to a suspension of estrone (1:352 g, 5.0 mmol) and 4-cyano-benzaldehyde (655 mg, 5.0 mmol) in ethanol (40 mL). The resulting orange solution was stirred for 4 hours at room temperature, then acetic acid (5 mL) and water (5 ml) were added (colour changes to yellow). 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: 1.795 g (94%) pale yellow solid. 1H-NMR (DMSO-d6, 400 MHz). δ: 0.91 (s, 3H, —CH3), 1.30-1.66 (m, 5H), 1.82-1.90 (m, 1H), 1.94-2.02 (m, 1H), 2.14-2.22 (m, 1H), 2.30-2.38 (m, 1H), 2.58-2.92 (m, 3H), 6.45 (d, J=2.3 Hz, 1H), 6.51 (dd, J=8.6, 2.3 Hz, 1H), 7.04 (d, J=8.6 Hz, 1H), 7.36 (s, 1H), 7.82 (d, J=8.6 Hz, 2H), 7.90 (d, J=8.6 Hz, 2H), 9.03 (s, 1H, —OH). LRMS (FAB+): 384.1 (100, [M+H]+). LRMS (FAB−): 383.2 (100, [M]−).

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-ad49cce10d09420bbe2944cc38d037b6
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08003783B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes