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

HRID 357233

반응식

HRID 357233 반응식
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

참가 물질

11

반응물 6

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

반응 조건

온도
-78 °C

실험 절차

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 1.7M 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 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.

후처리

  1. temperatureto warm to -40° C. over a period of 30 min
  2. stirringAfter stirring for 1 h
  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

출처 및 근거

ORD 기록
ord-0b462194545542c6a12333c590a0d785
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840746

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