Ethyl Acetate → Ethyl-6-[5 5-dimethyl-5,6-dihydro-naphthlen-8(7H)-one-2-yl]-naphthalen-2-oate

HRID 1289307Notes

Reaction equation

HRID 1289307 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][CH:9]([OH:12])[C:8]2[CH:7]=[C:6]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:17]=[CH:16]4)[CH:5]=[CH:4][C:3]1=2.C[N+]1([O-])CCOCC1.C(OCC)(=O)C>C(Cl)Cl.O.CCCCCC>[CH2:26]([O:25][C:23]([C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:6]3[CH:5]=[CH:4][C:3]4[C:2]([CH3:28])([CH3:1])[CH2:11][CH2:10][C:9](=[O:12])[C:8]=4[CH:7]=3)[CH:14]=2)[CH:19]=1)=[O:24])[CH3:27]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 15462839Ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxynaphth-2-yl]naphth-2-oate2×

Product 1

HCID 15887389Ethyl-6-[5 5-dimethyl-5,6-dihydro-naphthlen-8(7H)-one-2-yl]-naphthalen-2-oate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 101 mg (0.27 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-7-yl]naphth-2-oate (Compound B4) in 1.5 mL of methylene chloride was added 50 mg (0.43 mmol) of N-methylmorpholine N-oxide and 6.0 mg (0.017 mmol) of tetrapropylammonium perruthenate(VII). The reaction was stirred at room temperature for 3 h, diluted with water, and extracted with CH2 Cl2 (2 x). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give a foam. The title compound was obtained as a white solid after flash chromatography (silica, 10% ethyl acetate in hexane).

Workup

  1. extractionextracted with CH2 Cl2 (2 x)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a foam

Sources & evidence

ORD record
ord-a84be97286704aa0837da48449a7511c
Source dataset
uspto-grants-1998_05
Patent number
US05747542

Reaction notes

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