Chloromethyl Methyl Ether → HCID 13114595, compound

HRID 2092017Notes

Reaction equation

HRID 2092017 reaction equation
[CH3:1][C:2]1([CH3:11])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH:5]=[C:6]2[CH2:9][OH:10].C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23]Cl.C(=O)([O-])O.[Na+]>ClCCl>[CH3:21][O:22][CH2:23][O:10][CH2:9][C:6]1[CH:7]2[CH2:8][CH:3]([CH2:4][CH:5]=1)[C:2]2([CH3:11])[CH3:1]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 10582Bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-HCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 13114595HCID 13114595, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

rac-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol (10.0 g, 65.7 mmol), diisopropylethylamine (17.0 mL, 97.6 mmol) and chloromethyl methyl ether (6.5 mL, 85.6 mmol) were stirred in dichloromethane (100 mL) at room temperature for 1 day. After completion of the reaction, the reaction solution was mixed with saturated sodium hydrogen carbonate and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=10/1) to give the desired product (100% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=10/1)

Sources & evidence

ORD record
ord-d852140231524b7d8b7cfc3fbd9e1b4f
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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