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

HRID 481209

Reaction equation

HRID 481209 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 CH2Cl2 (2×). 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 CH2Cl2 (2×)
  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-a012689c071643cda4591fbc5aabbac8
Source dataset
uspto-grants-2003_11
Patent number
US06653483B1

Linked notes

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