Chloromethyl Methyl Ether → HCID 86688864, compound

HRID 2176205Notes

Reaction equation

HRID 2176205 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:26])[CH2:16][CH:17]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)[OH:18])([CH3:13])([CH3:12])[CH3:11].[CH3:27][O:28][CH2:29]Cl>C(Cl)Cl>[C:10]([O:14][C:15](=[O:26])[CH2:16][CH:17]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)[O:18][CH2:27][O:28][CH3:29])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 15508715HCID 15508715, compound

Product 1

HCID 86688864HCID 86688864, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

66 g of diisopropyl ethyl amine was dropped to a solution prepared by dissolving 100 g of 3-bicyclo[2.2.1]hept-5-en-2-yl-3-hydroxy-propionic acid tert-butyl ester (BHP) i and 44 g of chloromethyl methyl ether ii in 1 L of methylene chloride while stirring at room temperature. The mixture was stirred at room temperature for 4 hours, and reaction was evaluated by thin-layer chromatography (TLC) and terminated. This was followed by workup twice with 400 ml of each of a 1 N HCl solution and a 10% Na2CO3 solution, the resultant was washed with 400 ml of distilled water, and an organic layer was collected. Methylene chloride was removed from the organic layer at reduced pressure to obtain 96 g of 3-bicyclo[2,2,1]hept-5-en-2-yl-3-methoxymethoxy-propionic acid t-butyl ester iii (Yield: 81%). The structure was identified using 1H NMR.

Workup

  1. customprepared
  2. stirringThe mixture was stirred at room temperature for 4 hours
  3. customreaction
  4. customterminated
  5. washa 10% Na2CO3 solution, the resultant was washed with 400 ml of distilled water
  6. customan organic layer was collected
  7. customMethylene chloride was removed from the organic layer at reduced pressure

Sources & evidence

ORD record
ord-9de690f2749a4dd5a66be1c63504868d
Source dataset
uspto-grants-2015_06
Patent number
US09063411B2

Reaction notes

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