Ethanethiol → 4-(2-carbethoxy-1-ethyl)-7-hydroxy-2-oxo-2H-1-Benzopyran

HRID 6238

Reaction equation

HRID 6238 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].CCS.[C:8]([CH2:13][CH2:14][C:15]1[C:20]2[CH:21]=[CH:22][C:23]([O:25]C)=[CH:24][C:19]=2[O:18][C:17](=[O:27])[CH:16]=1)([O:10][CH2:11][CH3:12])=[O:9]>ClCCl>[C:8]([CH2:13][CH2:14][C:15]1[C:20]2[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:19]=2[O:18][C:17](=[O:27])[CH:16]=1)([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 867472394-(2-carbethoxy-1-ethyl)-7-methoxy-2-oxo-2H-1-Benzopyran

Product 1

HCID 124771144-(2-carbethoxy-1-ethyl)-7-hydroxy-2-oxo-2H-1-BenzopyranYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 726 mg (5.4 mmol) of AlCl3 in 10 mL of dichloromethane at 0° C. was added 4 mL of EtSH. The suspension became a clear solution within seconds. Then, 298 mg (1.08 mmol) of 3 in 4 mL of dichloromethane was added, turning the yellow solution red in color. The ice bath was removed, and the reaction stirred to room temperature for 3 h. The solvents were removed in vacuo, and the residue thoroughly vacuum dried. The residue was extracted into EtOAc as much as possible, then the extract was flash chromatographed using 30/70 EtOAc/hexane. The long- and short-wave UV active band gave 76.7 mg (27%) of 4.

Workup

  1. customThe ice bath was removed
  2. customThe solvents were removed in vacuo
  3. customthe residue thoroughly vacuum dried
  4. extractionThe residue was extracted into EtOAc as much as possible, then the extract
  5. customchromatographed

Sources & evidence

ORD record
ord-4f75d89850dd4de3a07f2755539ba444
Source dataset
uspto-grants-1993_09
Patent number
US05247099

Linked notes

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