Triethylamine → Ethyl [4-(tetrahydropyran-4-ylsulfanyl)phenyl]acetate

HRID 729704Notes

Reaction equation

HRID 729704 reaction equation
CCN(CC)CC.I[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[CH2:15]([O:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1)[CH3:16]>CN(C=O)C>[CH2:15]([O:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:22][CH:21]=1)[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27955064-iodotetrahydro-2H-pyranHCID 123300434-Mercapto-phenyl-acetic acid ethyl ester

Product 1

HCID 58860815Ethyl [4-(tetrahydropyran-4-ylsulfanyl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NEt3 (1.3 mL, 9.0 mmol) and 4-iodotetrahydropyran (1.93 g, 9.0 mmol) were added to a stirred solution of ethyl(4-mercaptophenyl)acetate (1.21 g, 6.0 mmol) in anhydrous DMF (10 mL) at 0° C. The mixture was allowed to warm to room temperature over 3 d, then the solvents were removed under reduced pressure. The residue was partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (50 mL), the aqueous phase being extracted further with Et2O (45 mL). The combined ethereal extracts were washed with H2O (50 mL), H2O-saturated aqueous Na2CO3 (1:1, 50 mL), and brine (50 mL), before being dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (IH-Et2O, 10:1 to 2:1) afforded the title compound: RF (IH-Et2O, 2:1)=0.31.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (50 mL)
  3. extractionthe aqueous phase being extracted further with Et2O (45 mL)
  4. washThe combined ethereal extracts were washed with H2O (50 mL), H2O-saturated aqueous Na2CO3 (1:1, 50 mL), and brine (50 mL)
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationFiltration, solvent evaporation, and flash chromatography (IH-Et2O, 10:1 to 2:1)

Sources & evidence

ORD record
ord-7a710407978a4f4287ad8295cf4d02bb
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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