Potassium Carbonate → Ethyl 4-[(thiochroman-8-YL)oxy]butyrate

HRID 1491803Notes

Reaction equation

HRID 1491803 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1216173,4-dihydro-2H-1-benzothiopyran-8-ol

Product 1

HCID 20093602Ethyl 4-[(thiochroman-8-YL)oxy]butyrateYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Under argon and with stirring, 1.5 g (9.02 mmol) of 8-thiochromanol are dissolved in 5 cm3 of dimethylformamide (DMF). 3.74 g (27.06 mmol) of K2CO3 are added and then 1.94 g (9.92 mmol) of ethyl 4-bromobutyrate dissolved in 6 cm3 of DMF are added dropwise. The mixture is heated at 60° C. for 5 hours. The DMF is evaporated off. The residue is taken up in H2O. The product is extracted with CH2Cl2 and then dried over MgSO4. Purification over a silica column (eluant: ether/petroleum ether 3:7) yields 2.48 g of the title compound (white solid).

Workup

  1. additionare added dropwise
  2. customThe DMF is evaporated off
  3. extractionThe product is extracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. customPurification over a silica column (eluant: ether/petroleum ether 3:7)

Sources & evidence

ORD record
ord-cedd4fc5155741c899a5080e9492150d
Source dataset
uspto-grants-1994_12
Patent number
US05371103

Reaction notes

Loading…