Ethanol → HCID 22722477, compound

HRID 1977962Notes

Reaction equation

HRID 1977962 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:5]=[C:6]([CH:18]=1)[O:7][CH2:8][CH2:9][O:10]C1C=CC=CC=1C.C(O)C>[Pd].O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([O:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([CH3:32])(=[O:30])=[O:31])(=[O:22])=[O:21])[CH:5]=[C:6]([CH:18]=1)[O:7][CH2:8][CH2:9][OH:10]

Participants

5

Reactant 2

HCID 702EthanolHCID 54200755HCID 54200755, compound

Product 1

HCID 22722477HCID 22722477, compoundYield 103.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[5-methyl-3-(2-(methylsulfonyl)phenylsulfonyloxy)phenoxy]ethoxytoluene (480 mg, 1.01 mmol), as prepared in the preceding step, 10% palladium on activated carbon (48.2 mg, ethanol (2 mL) and tetrahydrofuran (9 mL) was stirred at ambient temperature under hydrogen (balloon) for 45 minutes. The mixture was filtered through Celite and the filtrate was concentrated to give the title compound (404 mg, quantitative) as a colorless gum. 1H-NMR (300 MHz, CDCl3) δ8.45 (dd, 1H, J=7.8, 1.4 Hz), 8.13 (dd, 1H, J=7.8, 1.4 Hz), 7.88 (td, 1H, J=7.7, 1.4 Hz), 7.75 (td, 1H, J=7.7, 1.4 Hz), 6.60-6.66 (m, 3H), 3.77-3.98 (m, 4H), 2.25 (s, 3H), 1.95 (t, 1H, J=6 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C16H18O7S2: 409.0 (M+Na). Found: 408.7.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8556ed06c3e14ad3accffe8cebd808cd
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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