Chlorotrimethylsilane → 2-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran

HRID 1019190Notes

Reaction equation

HRID 1019190 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.[O:20]1[CH2:24][CH:23]=[CH:22][C:21]1=[O:25].[CH3:26][Si:27](Cl)([CH3:29])[CH3:28].C([O-])(O)=O.[Na+]>CCOCC.C1COCC1.[Cu]I.CCN(CC)CC>[CH3:26][Si:27]([CH3:29])([CH3:28])[O:25][CH:21]1[CH2:22][CH:23]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=2)[CH2:24][O:20]1

Participants

11

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8003PentaneHCID 103412(5H)-FuranoneHCID 660374-BromothioanisoleHCID 516892Sodium BicarbonateHCID 178418306HCID 178418306, compound

Product 1

HCID 184001922-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3.86 g (19 mmol) of 4-bromothioanisole in 90 mL of Et2O cooled at −78iC, is added 22 mL of 1.7 M solution of t-BuLi in pentane (38 mmol) dropwise. The reaction mixture is stirred for 15 min at −78 iC and 3.8 g of CuI is added and the reaction mixture is allowed to warm to −40 iC over a period of 30 min. A solution of 1.7 g of 2(5H)-furanone in 10 ml of THF is added. After stirring for 1 h, 2 ml of freshly distilled TMSCl is added dropwise. The reaction mixture is then treated with 2 ml of Et3N and 50 ml of sat. NaHCO3, and extracted with 100 ml of ether. The ether layer is dried over Na2SO4 and concentrated to the crude title compound which is used for the next step without further purification.

Workup

  1. additionis added
  2. temperatureto warm to −40 iC over a period of 30 min
  3. extractionextracted with 100 ml of ether
  4. dry with materialThe ether layer is dried over Na2SO4
  5. concentrationconcentrated to the crude title compound which
  6. customis used for the next step without further purification

Sources & evidence

ORD record
ord-44129519bb2a4d66accb27ce52159452
Source dataset
uspto-grants-2002_11
Patent number
US06486194B2

Reaction notes

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