Phenol → Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-(phenoxymethyl)-3-furanyl]-ester

HRID 1290355Notes

Reaction equation

HRID 1290355 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.FC(F)(F)S(O[CH2:23][C@@H:24]1[O:28][CH2:27][C@@H:26]([S:29][C:30](=[O:32])[CH3:31])[CH2:25]1)(=O)=O>C(Cl)Cl>[O:7]([CH2:23][C@@H:24]1[O:28][CH2:27][C@@H:26]([S:29][C:30](=[O:32])[CH3:31])[CH2:25]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 81531DiisopropylethylamineHCID 86750748Ethanethioic acid trans(+/-)-S-[tetrahydro-5-[[[(trifluoromethyl)sulfonyl]oxy]methyl]-3-furanyl]ester

Product 1

HCID 86750316Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-(phenoxymethyl)-3-furanyl]-esterYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 0.326 g of phenol, 1.8 ml of Hunig's base, and 2.5 ml of methylene chloride is added, via syringe, 1.07 g of product from Example 22 in 0.50 ml of methylene chloride. The reaction is stirred in an ice bath for 50 minutes; during which time the progress of reaction is checked by thin layer chromatography. The mixture is concentrated in vacuo, dissolved in ethyl acetate and washed with sodium bicarbonate. The organic layer is dried, concentrated in vacuo, and purified by chromatography (Silica Gel: 30% ethyl acetate/hexane) to give 0.532 g of the desired product.

Workup

  1. customduring which time the progress of reaction
  2. concentrationThe mixture is concentrated in vacuo
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with sodium bicarbonate
  5. customThe organic layer is dried
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography (Silica Gel: 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ac992664eaa1462787b8a84cbdaa183b
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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