Dimethyl Sulfate → HCID 15293880, compound

HRID 2399393Notes

Reaction equation

HRID 2399393 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#[N:2].[CH3:24]C(C)([O-])C.[K+].S(OC)(OC)(=O)=O.[Cl-].[NH4+]>CN(C)C=O>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][CH2:7][C:6]([O:9][CH3:24])=[CH:5][CH2:4]1)#[N:2]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 25517Ammonium ChlorideHCID 9861604SB-200473HCID 23665647Potassium tert-butoxide

Product 1

HCID 15293880HCID 15293880, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.3 g, 0.96 mmol) in dimethylformamide (3 mL) at 0° C. under an argon atmosphere was added potassium t-butoxide (0.11 g, 0.96 retool) and, 0.5h later, dimethyl sulfate (0.09 mL, 0.96 mmol). After 5 min, ammonium chloride was added, the mixture was extracted three times with ether, the organic extract was washed three times with water, once with brine, was dried (magnesium sulfate) and evaporated. Purification by flash chromatography, eluting with 9:1 hexanes/ethyl acetate, provided a white solid (0.06 g, 19%): m.p. 123°-125° C. Analysis Calc. for C20H25NO3 ·0.35 H2O:C 71.98, H 7.76, N 4.20; found: C 71.98, H 7.66, N 3.95

Workup

  1. extractionthe mixture was extracted three times with ether
  2. extractionthe organic extract
  3. washwas washed three times with water
  4. dry with materialonce with brine, was dried (magnesium sulfate)
  5. customevaporated
  6. customPurification by flash chromatography
  7. washeluting with 9:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-577a22f8b837417b9e4e688168d106f6
Source dataset
uspto-grants-1995_09
Patent number
US05449687

Reaction notes

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