Chloromethyl Methyl Ether → HCID 66760346, compound

HRID 1850395Notes

Reaction equation

HRID 1850395 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][O:9][CH3:10].[OH:11][C:12]1[C:20]2[O:19][C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[C:16]=2[C:15]([CH3:24])=[CH:14][C:13]=1[CH3:25].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CN(C=O)C>[CH3:10][O:9][CH2:8][O:11][C:12]1[C:20]2[O:19][C:18]([CH3:21])([CH3:22])[C:17](=[O:23])[C:16]=2[C:15]([CH3:24])=[CH:14][C:13]=1[CH3:25]

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 66759870HCID 66759870, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66760346HCID 66760346, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (1.23 g, 8.92 mmol) and chloromethylmethylether (539 mg, 6.69 mmol) were sequentially added to a suspension of DMF (20 mL) containing 7-hydroxy-2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one (920 mg, 4.46 mmol) synthesized in Reference Example 69 at 0° C. The reaction solution was warmed to room temperature and stirred for 15 hours. The resulting mixture was poured into saturated sodium bicarbonate water, and extraction was performed using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 85/15) to give 920 mg of the title compound (yield: 82%).

Workup

  1. customsynthesized in Reference Example 69 at 0° C
  2. washThe extract was washed with saturated saline
  3. customdried
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 85/15)

Sources & evidence

ORD record
ord-e6c10dc8c85b45c9b99c27ef84b57409
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

Loading…