Ethanol → HCID 15073462, compound

HRID 1521817Notes

Reaction equation

HRID 1521817 reaction equation
C(O[C:4](=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])C.[O-]CC.[Na+].CCO.[S:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:28])[CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[O:10]=[C:4]([CH:20]1[C:21](=[O:28])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:18][CH2:19]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 19048Thiochroman-4-oneHCID 2723922Sodium ethoxide

Product 1

HCID 15073462HCID 15073462, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of diethyloxalate (30.9 mL; 228.34 mmol; 1.5 eq.) in toluene (250 mL) is added dropwise at 0° C. to a solution of sodium ethoxide 21% w/w in EtOH (9.87 g; 182.67 mmol; 2 eq.). A solution of thiochroman-4-one (25 g; 152.23 mmol; 1 eq.) in toluene (250 mL) is added dropwise at 0° C. and the reaction mixture is allowed to warm up to rt. After overnight stirring, the solvent is removed and DCM (200 mL) and water (200 ml) are added. The aqueous phase is washed with DCM then acidified to pH=1-2 with 5N HCl (˜50 mL). The product is extracted with EtOAc (2×200 mL). The organic phases are combined, dried over MgSO4 and the solvent evaporated to afford 39.4 g (98%) of the title compound as an orange oil. MS (ESI+): 265.9.

Workup

  1. customthe solvent is removed
  2. additionDCM (200 mL) and water (200 ml) are added
  3. washThe aqueous phase is washed with DCM
  4. extractionThe product is extracted with EtOAc (2×200 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-4a8a49ad27e5494996ee495ea8df0b80
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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