2,2-Dimethoxypropane → HCID 86756341, compound

HRID 1611020Notes

Reaction equation

HRID 1611020 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CO[C:21](OC)([CH3:23])[CH3:22].[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:22][CH:21]([NH:1][C:2]1[S:3][C:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:23]

Participants

8

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 3792137ethyl 2-amino-5-benzylthiophene-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 86756341HCID 86756341, compound

Reagents, catalysts & solvents 4

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-amino-5-(phenylmethyl)thiophene-3-carboxylic acid, ethyl ester (2.61 g) and 4-methylbenzenesulfonic acid (30 mg) in dry toluene (50 ml) was added 2,2-dimethoxypropane. The solution was heated to reflux for 5 hours and then allowed to cool to ambient temperature. A solution of sodium borohydride (800 mg) in ethanol (100 ml) was added to the solution and the mixture was stirred at room temperature under nitrogen for 24 hours. The mixture was diluted with water and then extracted thrice with ethyl acetate. The combined organic extracts were washed with brine and then dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to give an oil. The residue was purified by column chromatography over silica, eluting with diethyl ether:isohexane (1:19) to give the subtitle compound (550 mg).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 hours
  3. extractionextracted thrice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an oil
  9. customThe residue was purified by column chromatography over silica
  10. washeluting with diethyl ether:isohexane (1:19)

Sources & evidence

ORD record
ord-e427281a7db847d3a1b857e2a40793ec
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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