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Hydrochloric Acid → 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

HRID 1631896
Notes
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Reaction equation

HRID 1631896 reaction equation
[CH3:1][O:2][C:3]1[CH2:7][CH2:6][C:5](=[O:8])[C:4]=1[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17].C([N-]C(C)C)(C)C.[Li+].[CH3:26][O:27][CH:28]1[CH2:33][CH2:32][CH:31]([CH:34]=[O:35])[CH2:30][CH2:29]1.Cl>O1CCCC1.O>[OH:35][CH:34]([CH:31]1[CH2:32][CH2:33][CH:28]([O:27][CH3:26])[CH2:29][CH2:30]1)[CH:6]1[C:5](=[O:8])[C:4]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])=[C:3]([O:2][CH3:1])[CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2979194-Methoxycyclohexane-1-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 155776462-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

Product 1

HCID 668669535-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (2 g, 8.7 mmol) in dry tetrahydrofuran (25 ml) at −78° C. is added a solution of lithium diisopropylamide (5.8 ml, 10.4 mmol, 1.8 M in hexane/THF/ethylbenzene) dropwise over 20 minutes. The resultant solution is stirred for 30 minutes at −78° C. before adding 4-methoxy-cyclohexanecarbaldehyde (1.4 g, 9.8 mmol) dissolved in tetrahydrofuran (15 ml). The reaction mixture is allowed to warm to room temperature overnight then diluted with water, acidified with 2 N HCl and extracted with ethyl acetate (3×15 ml). The combined organic extract are dried over magnesium sulfate, filtered and evaporated under reduced pressure to give an brown oil. The residue is purified by flash chromatography to 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.7 g).

Workup

  1. extractionextracted with ethyl acetate (3×15 ml)
  2. extractionThe combined organic extract
  3. dry with materialare dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give an brown oil
  7. customThe residue is purified by flash chromatography to 5-[Hydroxy-(4-methoxy-cyclohexyl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.7 g)

Sources & evidence

ORD record
ord-266e89607b93468694c448d05d8508de
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791303B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes