Methanol → HCID 19375608, compound

HRID 2211112Notes

Reaction equation

HRID 2211112 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:7][CH2:8][C:9]([CH3:12])([CH3:11])[N:10]=2)=[CH:2]1.C([Li])(CC)C.[C:18]1([C:23](Cl)=[O:24])[S:22][CH:21]=[CH:20][CH:19]=1.CO>CCOCC.O1CCCC1>[C:18]1([C:23]([C:2]2[S:1][CH:5]=[CH:4][C:3]=2[C:6]2[O:7][CH2:8][C:9]([CH3:12])([CH3:11])[N:10]=2)=[O:24])[S:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 789282-Thiophenecarbonyl chlorideHCID 12694430HCID 12694430, compoundHCID 178418400CID 53628100

Product 1

HCID 19375608HCID 19375608, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of 2-(3-thienyl)-4,4-dimethyloxazoline was dissolved in 50 ml of ether, and 10 ml of s-butyllithium (1.3M, cyclohexane solution) was added dropwise thereto at -70° C. The solution was stirred for 1 hour. The reaction solution was added dropwise to a solution of 2.4 g of 2-thenoyl chloride in 50 ml of tetrahydrofuran at -78° C., and the solution was stirred for 30 minutes. Thereafter, 1 ml of methanol was added to the solution, and the reaction solution was concentrated. After adding water thereto, the solution was extracted with chloroform. The chloroform layer was dried and concentrated, and the residue was purified by silica gel chromatography to obtain 2.8 g of 2-(2-thenoyl)-3-(4,4-dimethyl-2-oxazoline-2-yl)thiophene.

Workup

  1. customat -70° C
  2. stirringthe solution was stirred for 30 minutes
  3. concentrationthe reaction solution was concentrated
  4. additionAfter adding water
  5. extractionthe solution was extracted with chloroform
  6. dry with materialThe chloroform layer was dried
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-60e3e00f38ba4cd7b7559c8be7bda3ac
Source dataset
uspto-grants-1995_10
Patent number
US05462941

Reaction notes

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