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Water → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-aminophenylethynyl)cyclohexan-1-one

HRID 343548
Notes
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Reaction equation

HRID 343548 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=4)[CH2:20][CH2:19][C:18]4(OCC[O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[NH4+].C(=O)([O-])[O-].[Na+].[Na+]>CO.C(O)(=O)C.[Cl-].[Cl-].[Cl-].[Ti+3].ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 153920294-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(4-nitrophenylethynyl)cyclohexane

Product 1

HCID 98441184-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-aminophenylethynyl)cyclohexan-1-one

Reagents, catalysts & solvents 4

HCID 10313229titanium(III) trichlorideCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(4-nitrophenylethynyl)cyclohexane (0.19 g, 0.40 mmol) in methanol (1 mL), acetic acid (1.2 mL), and water (1.2 mL) under an argon atmosphere was added titanium trichloride (0.3 g, 2 mmol). After stiring for 1.5 h at room temperature, water (1.2 mL) and ammonium hydroxide (2.5 mL) were added. After stirring an additional 1 h, methanol (17.5 mL), 5% sodium carbonate (17.5 mL) and dichloromethane (35 mL) were added, and stirring was continued for 3 days. The suspension was filtered through Celite®, was washed well with dichloromethane, and was evaporated. Water was added, the mixture was extracted three times with dichloromethane, the extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 3:7 ethyl acetate:hexanes, provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(4-aminophenylethynyl)cyclohexan-1-one as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ 7.28 (d, J=8.4 Hz, 2H), 7.24 (d, J=2.1 Hz, 1H), 7.12 (d, J=8.5 Hz, 1H), 6.85 (d, J=8.5 Hz, 1H), 6.64 (d, J=8.1 Hz, 2H), 4.80 (m, 1H), 3.85 (s, 3H), 3.05 (dt, J=14.3, 4.1 Hz, 2H), 2.45 (br d, J=14.6 Hz, 2H), 2.29 (m, 4H), 1.8-2.0 (m, 6H), 1.61 (m, 2H).

Workup

  1. stirringstirring
  2. waitwas continued for 3 days
  3. filtrationThe suspension was filtered through Celite®
  4. washwas washed well with dichloromethane
  5. customwas evaporated
  6. additionWater was added
  7. extractionthe mixture was extracted three times with dichloromethane
  8. dry with materialthe extract was dried (magnesium sulfate)
  9. customwas evaporated
  10. customPurification by flash chromatography
  11. washeluting with 3:7 ethyl acetate

Sources & evidence

ORD record
ord-f8b7832455a84721a42fbfed74e0cc47
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05861421

Reaction notes

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