HCID 19363263, compound → HCID 19363347, compound

HRID 850495Notes

Reaction equation

HRID 850495 reaction equation
CC1(C)C[O:5][C:4]([C:7]2[C:12]([CH2:13][OH:14])=[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:10]([O:21][CH3:22])=[CH:9][CH:8]=2)=N1>Cl>[CH3:22][O:21][C:10]1[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:4](=[O:5])[O:14][CH2:13]2

Participants

3

Reactant 1

HCID 19363263HCID 19363263, compound

Product 1

HCID 19363347HCID 19363347, compoundYield 97,030.203%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

[6-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)-3-methoxy-2-pentyloxyphenyl]-methanol (4.69 g, 0.014 mmol, 1 eq) was dissolved in 3N hydrochloric acid (50 ml), and the solution was stirred under heating for 3 hours. After the completion of the reaction, the mixture was cooled to room temperature and extracted twice with diethyl ether (50 ml). The organic layers were combined, washed with saturated brine (100 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2/1) to give 5-methoxy-4-pentyloxy-3H-isobenzofuran-1-one (3.4 g, 82.4%) as a colorless oil.

Workup

  1. temperatureunder heating for 3 hours
  2. customAfter the completion of the reaction
  3. extractionextracted twice with diethyl ether (50 ml)
  4. washwashed with saturated brine (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-306a9b9b32294a4abf50da8a79f6f73e
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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