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

HRID 1107881Notes

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

Conditions

Temperature: -78 °C

Procedure

To a solution of 3.86 g (19 mmol) of 4-bromothioanisole in 90 mL of Et2O cooled at -78° C., is added 22 mL of a 1.7 M solution of t-BuLi in pentane (38 mmol) dropwise. The reaction mixture is stirred for 15 min at -78° C. and 3.8 g of CuI is added and the reaction mixture is allowed to warm to -40° C. 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 Et2O. The Et2O layer is dried over Na2SO4 and concentrated to give the crude title compound which is used for the next step without further purification.

Workup

temperatureto warm to -40° C. over a period of 30 min
stirringAfter stirring for 1 h
extractionextracted with 100 mL of Et2O
dry with materialThe Et2O layer is dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-c5e3114fff2240f386d9e34de3694f76
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063811

Reaction notes

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