Chloromethyl Methyl Ether → HCID 58604072, compound

HRID 2113663Notes

Reaction equation

HRID 2113663 reaction equation
[Br:1][C:2]1[C:3](=[O:21])[CH2:4][C:5]2([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([OH:16])[C:11]=3[Br:15])[C:6]=12.C(N(CC)C(C)C)(C)C.[CH3:31][O:32][CH2:33]Cl>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3](=[O:21])[CH2:4][C:5]2([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:16][CH2:31][O:32][CH3:33])[C:11]=3[Br:15])[C:6]=12

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 10364441HCID 10364441, compound

Product 1

HCID 58604072HCID 58604072, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,6-dibromo-3a-butyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one (189 mg, 0.46 mmol) in anhydrous DMF (2.3 mL) was placed under a N2 atmosphere and stirred at room temperature while N,N-diisopropylethylamine (0.242 mL, 1.38 mmol) and chloromethyl methyl ether (0.070 mL, 0.92 mmol) were added successively. After stirring at room temperature for 16 hours, the mixture was diluted with EtOAc and washed with 1N HCl. The organic phase was washed with 5% NaHCO3 and brine, dried over MgSO4, filtered, and concentrated under vacuum to provide crude 1,6-dibromo-3a-butyl-7-(methoxymethoxy)-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as an oil.

Workup

  1. additionwere added successively
  2. washwashed with 1N HCl
  3. washThe organic phase was washed with 5% NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4ce87f0bd89149ed8fdcbec3f0ac1935
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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