Chloromethyl Methyl Ether → HCID 67227478, compound

HRID 624370Notes

Reaction equation

HRID 624370 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[O:5][C:6]1[CH:16]=[C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[CH2:26][C:25]=3[C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[CH2:19][CH2:18]2)[CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:42][O:43][CH2:44]Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([C:25]2[CH2:26][C:27]([CH3:30])([CH3:31])[CH2:28][CH2:29][C:24]=2[CH2:23][N:20]2[CH2:19][CH2:18][N:17]([C:15]3[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([O:5][C:4]4[CH:39]=[CH:40][CH:41]=[C:2]([O:1][CH2:42][O:43][CH3:44])[CH:3]=4)[CH:16]=3)[CH2:22][CH2:21]2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 10796Cesium carbonateHCID 67226950HCID 67226950, compound

Product 1

HCID 67227478HCID 67227478, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of EXAMPLE 176B (0.295 g), methoxymethyl chloride (0.117 mL) and cesium carbonate (0.334 g) in N,N-dimethylformamide (3 mL) was stirred at 60° C. for 16 hours. The reaction mixture was partitioned between dichloromethane and water. The water layer was extracted with dichloromethane. The combined organic extracts were washed with water (2×), dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromotography (silica gel, 5%-20% ethyl acetate/hexanes) providing the product.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. extractionThe water layer was extracted with dichloromethane
  3. washThe combined organic extracts were washed with water (2×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromotography (silica gel, 5%-20% ethyl acetate/hexanes)
  8. customproviding the product

Sources & evidence

ORD record
ord-deb1b9b09ff847a79de920144e60bc06
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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