Tetrahydrofuran → HCID 15747197, compound

HRID 896706Notes

Reaction equation

HRID 896706 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li][CH2:11][CH2:12][CH2:13]C.CC1C=CC([CH:20]=[S:21])=CC=1.[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>[Cl-].[NH4+].C(OCC)(=O)C>[CH3:9][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH:26]([C:25]2[CH:24]=[CH:28][C:13]([S:21][CH3:20])=[CH:12][CH:11]=2)[OH:27])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 660374-BromothioanisoleHCID 181775354-MethylthiobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 15747197HCID 15747197, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 4-bromothioanisole (1.06 g, 5.2 mmol) in THF (20 mL) at −78° C. was added BuLi (2.3M, hexane, 2.2 mL, 5 mmol) dropwise. After 30 min at −78° C., 4-methylthiobenzaldehyde (685 mg, 4.5 mmol) was added. After 20 min., the resulting reaction mixture was diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 80:20) provided the bis-(4-methylsulfanyl-phenyl)-methanol compound.

Workup

  1. waitAfter 20 min.
  2. customthe resulting reaction mixture
  3. washThe organic extracts were washed (H2O, brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washby flash chromatography (eluting with hexane/ethyl acetate, 80:20)

Sources & evidence

ORD record
ord-83c33591c1834b089047ba3f4ca89cb3
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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