Acetic Acid → HCID 20708424, compound

HRID 430790Notes

Reaction equation

HRID 430790 reaction equation
[C:1]1([CH2:7][CH2:8][SH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][CH2:14][C:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([O:24][CH:25](C)[C:26]([O:28][CH3:29])=[O:27])[C:18]=2[O:17][CH:16]=1.[C:31](O)(=O)C>CN(C=O)C.O>[C:1]1([CH2:7][CH2:8][S:9][CH2:13][CH2:14][C:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:18]=3[O:17][C:16]=2[CH3:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 781262-PhenylethanethiolHCID 18351757HCID 18351757, compound

Product 1

HCID 20708424HCID 20708424, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2-phenylethanethiol (0.42 ml) was dissolved in DMF (5 ml) and sodium hydride (60%, 132 mg) was added to the obtained solution, followed by stirring the resulting mixture at room temperature for 40 minutes. To this reaction solution, a solution of methyl 3-(2-bromoethyl)-2-methyl-benzofuran-7-yloxyacetate (900 mg) in DMF (8 ml) was added dropwise and the resulting solution was stirred for 30 minutes. Acetic acid (0.5 ml) was added to the reaction solution and the solution was poured into water layer (100 ml), followed by extraction of the resultant twice with ethyl acetate (30 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: cyclohexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (1.03 g, yield: 98%).

Workup

  1. stirringthe resulting solution was stirred for 30 minutes
  2. extractionfollowed by extraction of the resultant twice with ethyl acetate (30 ml)
  3. washwashed with saturated brine
  4. dry with materialby drying over sodium sulfate
  5. customAfter removing the sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (solvent: cyclohexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-289a95cdb51342a98c5c0749d72a2a7f
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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