Chloromethyl Methyl Ether → HCID 58604074, compound

HRID 2113647Notes

Reaction equation

HRID 2113647 reaction equation
[CH2:1]([C:5]12[CH2:17][C:16](=[O:18])[CH:15]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([OH:14])=[CH:11][C:12]=1[CH2:13]2)[CH2:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.[CH3:28][O:29][CH2:30]Cl>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:5]12[CH2:17][C:16](=[O:18])[CH:15]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([O:14][CH2:28][O:29][CH3:30])=[CH:11][C:12]=1[CH2:13]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 58604056HCID 58604056, compound

Product 1

HCID 58604074HCID 58604074, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8a-butyl-6-hydroxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (300 mg, 1.2 mmol) in anhydrous DMF (3 mL) was placed under a N2 atmosphere and stirred at room temperature while N,N-diisopropylethylamine (0.63=L, 3.6 mmol) and chloromethyl methyl ether (0.183 mL, 2.4 mmol) were added successively. After stirring at room temperature overnight, the mixture was diluted with EtOAc (100 mL) and washed with 1N HCl. The acid wash was back-extracted with EtOAc. The combined organics were washed with 5% NaHCO3, water and brine, dried over MgSO4, filtered, and concentrated under vacuum to a brown oil. The crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7 cm) silica gel column, eluting with 5:1 hexane-EtOAc, to provide 8a-butyl-6-(methoxymethoxy)-8,8a-dihydrocyclopenta[a]inden-2(1H)-one as an oil.

Workup

  1. additionwere added successively
  2. washwashed with 1N HCl
  3. washThe acid wash
  4. extractionwas back-extracted with EtOAc
  5. washThe combined organics were washed with 5% NaHCO3, water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum to a brown oil
  9. customThe crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7 cm) silica gel column
  10. washeluting with 5:1 hexane-EtOAc

Sources & evidence

ORD record
ord-48af0ea73ed34249acbbe1f86caa5b33
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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