Dimethyl Sulfate → HCID 68790209, compound

HRID 2253276Notes

Reaction equation

HRID 2253276 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1.COC1C=C(C=C(C2C=CC(OC3C=CC(C=O)=CC=3)=CC=2)C(O)=O)C=C(OC)C=1.C([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O.[BH4-].[Na+]>C(O)C.CN(C=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:29][OH:30])=[CH:27][CH:28]=2)=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

8

Reactant 5

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 731978473-(3,5-Dimethoxyphenyl)-2-[4-(4-formylphenoxy)-phenyl]-acrylic acid methyl ester2×HCID 73856337HCID 73856337, compound

Product 1

HCID 68790209HCID 68790209, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

3-(3,5-dimethoxy-phenyl)-2-[4-(4-formylphenoxy)-phenyl]-acrylic acid methyl ester (21) was first prepared by converting the corresponding free acid (3) to the methyl ester by addition of DMF, K2CO3 and dimethyl sulfate in a manner analogous to Example 1 (f) above. Sodium borohydride (0.125 g, 3.3 mmol) was added to a suspension of 21 (1.26 g, 3 mmol) in ethanol (20 mL) and stirred at room temperature for 1 hr. The reaction was quenched with 5% aqueous HCl, and ethanol was evaporated under reduced pressure. Residue was taken up in ethyl acetate (50 mL) and washed with brine (2×20 mL), dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by silica gel chromatography and eluted with hexanes-ethyl acetate (1:1). Yield: 1.14 g, 95.0%. Analysis: 1HNMR (DMSO-d6): δ 7.72 (s, 1H), 7.36 (d, J=8.8 Hz, 2H), 7.19 (d, J=8.8 Hz, 2H), 7.01 (d, J=8.4 Hz, 2H), 6.99 (d, J=8.4 Hz, 2H), 6.41 (t, J=2.4 Hz, 1H), 6.28 (d, J=2.4 Hz, 2H), 5.18 (t, J=6.4 Hz, 1H), 4.49 (d, J=4.8 Hz, 2H), 3.72 (s, 3H), 3.57 (s, 6H).

Workup

  1. customThe reaction was quenched with 5% aqueous HCl, and ethanol
  2. customwas evaporated under reduced pressure
  3. washwashed with brine (2×20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluted with hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-9906b5bdeb064e88a255472d7ad9ba71
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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