(6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-ylidene)-acetic acid methyl ester → (6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester

HRID 339184Notes

Reaction equation

HRID 339184 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]=[C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[H][H]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 66650886(6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-ylidene)-acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 66651348(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl esterYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-ylidene)-acetic acid methyl ester (5.63 g, 15.8 mmol) was dissolved in 300 mL EtOAc in a 1 L Parr vessel, and 1.0 g of palladium/activated carbon was added. The reaction mixture was shaken for 8 hours under 50 psi of hydrogen, after which the mixture was filtered through a CELITE™ plug. The filtrate was evaporated under reduced pressure to give an oil, which was dissolved in hexanes:EtOAc (3:2) and eluted through silica gel to afford 5.22 g (14.56 mmol, 92.2%) of (6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester. MS: 359 (M+H)+.

Workup

  1. additionwas added
  2. filtrationafter which the mixture was filtered through a CELITE™ plug
  3. customThe filtrate was evaporated under reduced pressure
  4. customto give an oil, which
  5. washeluted through silica gel

Sources & evidence

ORD record
ord-85a10f30c1b7486485d43465bb5bd022
Source dataset
uspto-grants-2014_11
Patent number
US08889906B2

Reaction notes

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