Diethyl (methoxy(methoxycarbonyl)methyl)phosphonate → (Z)-2-Methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-acrylic Acid Methyl Ester

HRID 855955Notes

Reaction equation

HRID 855955 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4](P(OCC)(OCC)=O)[O:5][CH3:6].[Li+].C[O-].[CH3:19][C:20]1[O:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:31][CH2:32][O:33][C:34]1[C:42]2[CH:41]=[CH:40][S:39][C:38]=2[C:37]([CH:43]=O)=[CH:36][CH:35]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])/[C:4](/[O:5][CH3:6])=[CH:43]/[C:37]1[C:38]2[S:39][CH:40]=[CH:41][C:42]=2[C:34]([O:33][CH2:32][CH2:31][C:21]2[N:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:24][C:20]=2[CH3:19])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 4107971Diethyl (methoxy(methoxycarbonyl)methyl)phosphonateHCID 4177230Lithium methanolateHCID 111759364-[2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-1-benzothiophene-7-carbaldehyde

Product 1

HCID 11259455(Z)-2-Methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-acrylic Acid Methyl EsterYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 6.07 g (20.2 mmol) of (diethoxyphosphoryl)-methoxy acetic acid methyl ester (H. Gross, Justus Liebigs Ann. Chem. 1967, 707, 35-43), 0.86 g of lithium methylat (21.6 mmol) and 5.00 g of 4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-carbaldehyde (13.5 mmol) in 50 ml of DMF was heated for 21 h at 75° C. The suspension was cooled to 0° C., the solid filtered off and washed with 30 ml of cold (−15° C.) ethanol. The filter cake was dissolved in a mixture of 100 ml dichloromethane and 60 ml of water, the organic layer separated, dried over sodium sulfate and evaporated to dryness. Thereby, 3.45 g (55%) of the title compound with a purity of 91% (GC area) were obtained as white crystals.

Workup

  1. temperatureThe suspension was cooled to 0° C.
  2. filtrationthe solid filtered off
  3. washwashed with 30 ml of cold (−15° C.) ethanol
  4. dissolutionThe filter cake was dissolved in a mixture of 100 ml dichloromethane and 60 ml of water
  5. customthe organic layer separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-b138fe4938cb42f3a680b3e996bedc00
Source dataset
uspto-grants-2007_08
Patent number
US07262303B2

Reaction notes

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