Benzene → HCID 53683575, compound

HRID 486742Notes

Reaction equation

HRID 486742 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][S:9][C@@H:8]([CH2:11][SH:12])[CH2:7]1)=[O:5])[CH3:2].[O-]CC.[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC=CC=1>C(O)C>[CH2:17]([S:12][CH2:11][C@H:8]1[CH2:7][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][S:9]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 7498Benzyl BromideHCID 2723922Sodium ethoxideHCID 53870179HCID 53870179, compound

Product 1

HCID 53683575HCID 53683575, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of trans-4-ethoxycarbonyl-2-mercaptomethyltetrahydrothiophene (compound No. 15-1, 0.3 g) in ethanol (2 ml), sodium ethoxide (0.11 g) is added under nitrogen atmosphere and ice-cooling and the mixture is stirred for 30 minutes. Benzyl bromide (0.28 g) dissolved in ethanol (1 ml) was added to the mixture and the mixture is stirred for 30 minutes under ice-cooling and 1 hour at room temperature. Benzene is added to the reaction mixture. The organic layer is washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue is purified by a silica gel column chromatography to give titled compound (compound No. 25-1).

Workup

  1. temperatureice-cooling
  2. additionwas added to the mixture
  3. stirringthe mixture is stirred for 30 minutes under ice-
  4. washThe organic layer is washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue is purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-afe7127796ab4c1c833ca03a1c56a076
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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