Chloromethyl Methyl Ether → HCID 18973699, compound

HRID 1780858Notes

Reaction equation

HRID 1780858 reaction equation
[C:1]([CH:5]1[CH2:10][C:9]([C:24]#[N:25])([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:26])([O:3][CH3:4])=[O:2].[H-].[Na+].Cl[CH2:30][O:31][CH3:32]>CN(C)P(=O)(N(C)C)N(C)C>[C:1]([C:5]1[CH2:10][C:9]([C:24]#[N:25])([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:12]=2)[CH2:8][CH2:7][C:6]=1[O:26][CH2:30][O:31][CH3:32])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 15295197HCID 15295197, compound

Product 1

HCID 18973699HCID 18973699, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 2-carbomethoxy-4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)cyclohexan-1-one (1.0 g, 2.8 mmol) and sodium hydride (80% dispersion in mineral oil, 0.09 g, 3.1 mmol) in dry hexamethylphosphoric triamide (8 mL) was stirred under an argon atmosphere at room temperature for 0.5 h. Chloromethylmethyl ether (0.26 mL, 3.4 mmol) was added and stirring was continued for 4.5 h. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, was extracted three times, the organic layer was dried (sodium sulfate) and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, to provide a white solid (0.5 g, 44%): m.p. 98°-99° C.

Workup

  1. customThe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. extractionwas extracted three times
  3. dry with materialthe organic layer was dried (sodium sulfate)
  4. customthe solvent was removed in vacuo
  5. customThe product was purified by flash chromatography
  6. washeluting with 3:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6804fdfe8c744356820c81737a1c7433
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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