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

HRID 1770220Notes

Reaction equation

HRID 1770220 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-0634d158ca3548ebb427aa164f64bdda
Source dataset
uspto-grants-1995_01
Patent number
US05385930

Reaction notes

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