Chloromethyl Methyl Ether → HCID 86714336, compound

HRID 1771477Notes

Reaction equation

HRID 1771477 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:14].C([O-])([O-])=O.[K+].[K+].[CH2:21](Cl)[O:22][CH3:23]>CO.C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:14][CH2:21][O:22][CH3:23]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 184287461-Bromo-6-methoxynaphthalen-2-ol

Product 1

HCID 86714336HCID 86714336, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-bromo-6-methoxynaphthalen-2-ol (described in U.S. 61/423,799) (2.90 g, 11.5 mmol) in MeOH (20 mL) and THF (20 mL) was added K2CO3 (3.18 g, 23.0 mmol) and MOMCl (1.10 g, 13.8 mmol). The resulting mixture was stirred at 20° C. for 48 hours and stirred at 30-40° C. for 5 days. An aqueous/EtOAc workup was followed by purification by silica gel column chromatography (PE to PE/EtOAc=200/1) to give the product (1.90 g, yield 56%) as an off-white solid.

Workup

  1. stirringstirred at 30-40° C. for 5 days
  2. customAn aqueous/EtOAc workup was followed by purification by silica gel column chromatography (PE to PE/EtOAc=200/1)

Sources & evidence

ORD record
ord-a8a7dbe5ac7e42c6b4d03fa829cf7274
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

Loading…