Chloromethyl Methyl Ether → HCID 22571549, compound

HRID 2415594Notes

Reaction equation

HRID 2415594 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=[O:14])[CH3:13])=[CH:9][CH:10]=2)[C:5]([CH3:16])([CH3:15])[CH2:4][CH2:3]1.[CH3:17][O:18][CH2:19]Cl.C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:17][O:18][CH2:19][O:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=[O:14])[CH3:13])=[CH:9][CH:10]=2)[C:5]([CH3:16])([CH3:15])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 22571559HCID 22571559, compound

Product 1

HCID 22571549HCID 22571549, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (+/−) 1-hydroxy-6-acetyl-1,2,3,4-tetrahydro-4,4-dimethyl-naphthalene (Compound D25, 24.8 mg, 0.11 mmol), chloromethyl methyl ether (0.12 mmol), triethyl amine (0.02 ml, 0.13 mmol) and catalytic amount of tetrabutylammonium bromide in 2 ml of CH2Cl2 was stirred at room temperature for 5 h. Purification by column chromatography (silica) with ethyl acetate/hexane (1/10) afforded the title compound as an oil (17.8 mg).

Workup

  1. customPurification by column chromatography (silica) with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-e6df112be2aa45f38a56e292e07a75be
Source dataset
uspto-grants-2004_11
Patent number
US06818775B2

Reaction notes

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