Benzenesulfonic Acid → (5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl ester

HRID 514035Notes

Reaction equation

HRID 514035 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([CH3:14])[CH2:7][C:8]2=[O:13].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=O.C1(S(O)(=O)=O)C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:15](=[O:18])[CH:16]=[C:7]1[CH:6]([CH3:14])[CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[C:8]1=[O:13])[CH3:21]

Participants

6

Reactant 4

HCID 7371Benzenesulfonic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 70211Ethyl oxoacetateHCID 638208135-methoxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 86691539(5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a heavy walled sealed tube, 5-methoxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one (1.3 g, 6.8 mmol), ethyl glyoxylate (3 mL, 50% solution in toluene), benzenesulfonic acid (100 mg), magnesium sulfate (5 g), and toluene (30 mL) were heated to 120° C. for 13 hours. The reaction was cooled to room temp, filtered, diluted with water, and extracted with ethyl acetate. The extracts were washed with brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash column chromatography to yield the desired product (960 mg, 51% yield). LCMS-ESI+ (m/z): [M+H]+ calcd for C16H19O4: 275.13. Found: 275.26.

Workup

  1. filtrationfiltered
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-8295bf347f074328a42d1bb6a40f4a9a
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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