Ethanol → Ethyl 4-[3-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-oxo-propenyl]-benzoate

HRID 1453624Notes

Reaction equation

HRID 1453624 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH3:13][O:14][C:15]1[C:16]([C:29](=[O:31])[CH3:30])=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1.[CH2:32](O)C.Cl.CN(C)CCCN=C=NCC>[OH-].[Na+].CO.ClCCl.O>[CH3:13][O:14][C:15]1[C:16]([C:29](=[O:31])[CH:30]=[CH:1][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH2:10][CH3:32])=[O:8])=[CH:5][CH:4]=2)=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 15294Methyl 4-FormylbenzoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 30179161-(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthyl)ethan-1-one2×

Product 1

HCID 69037287Ethyl 4-[3-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-oxo-propenyl]-benzoateYield 32.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-formylbenzoate (185 mg, 1.13 mmol) was added to a solution of 1-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound 11, 293 mg, 1.13 mmol) in 5 mL of 1 N NaOH and 10 mL of methanol. After stirring at room temperature for 18 h, the reaction mixture was extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. The residue was then added to a solution of ethanol (520 mg, 11.30 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (433 mg, 2.26 mmol) and N,N-dimethylaminopyridine (DMAP) (13 mg, 0.11 mmol) in 5 mL of dichloromethane. After stirring at room temperature for 8 h, water (10 mL) was added and the mixture was extracted with ethyl acetate (3×5 mL), washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (80:20 hexane/ethyl acetate) afforded the title compound (153 mg, 32% yield) as a colorless oil:

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layer was washed with brine (1×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. stirringAfter stirring at room temperature for 8 h
  6. extractionthe mixture was extracted with ethyl acetate (3×5 mL)
  7. washwashed with brine (1×5 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated at reduced pressure
  10. customPurification by flash chromatography (80:20 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-34b81b41021d45c5b8dd43eb4562fa89
Source dataset
uspto-grants-2009_01
Patent number
US07476673B2

Reaction notes

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