(+/-)-7-Benzyloxy-1-(4-fluorophenoxy)-2-(2-methoxyethoxy-methoxy)-heptane → (+/-)-7-(4-Fluorophenoxy)-6-(2-methoxyethoxymethoxy)heptan-1-ol

HRID 413563Notes

Reaction equation

HRID 413563 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)C1C=CC=CC=1>C(O)C.[Pd]>[F:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH:14]([O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 18533445(+/-)-7-Benzyloxy-1-(4-fluorophenoxy)-2-(2-methoxyethoxy-methoxy)-heptane

Product 1

HCID 18533434(+/-)-7-(4-Fluorophenoxy)-6-(2-methoxyethoxymethoxy)heptan-1-olYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(±)-7-benzyloxy-1-(4-fluorophenoxy)-2-(2-methoxyethoxy-methoxy)-heptane 43 (11 g, 26.3 mmol) in 30 ml of ethanol is added to a 50 ml round bottom flask. Palladium on activated carbon (10% Pd/C, 150 mg) is added and the reaction mixture is stirred under an atmosphere of hydrogen. After 3 hours, the reaction mixture was filtered through celite, washed with ethanol and concentrated. The crude product was purified on silica gel (ethyl acetate:hexane 1:1) to give (±)-7-(4-fluorophenoxy)-6-(2-methoxyethoxymethoxy)heptan-1-ol 44 (7.9 g, 91%). The structure was confirmed by 1H-NMR.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washwashed with ethanol
  3. concentrationconcentrated
  4. customThe crude product was purified on silica gel (ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-400ef2a98e204e8c98c82aa95376f9e5
Source dataset
uspto-grants-2003_05
Patent number
US06566538B1

Reaction notes

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