2-Trimethylsilyl-1,3-dithiane → 2-((3S,5R)-3,5-Dimethyl-cyclohexylidene)-[1,3]dithiane

HRID 2055194

반응식

HRID 2055194 반응식
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.C([Li])CCC.[CH3:16][C@H:17]1[CH2:22][C@@H:21]([CH3:23])[CH2:20][C:19](=O)[CH2:18]1>C1COCC1>[CH3:16][C@H:17]1[CH2:22][C@@H:21]([CH3:23])[CH2:20][C:19](=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)[CH2:18]1

참가 물질

5

반응물 3

HCID 834132-Trimethylsilyl-1,3-dithianeHCID 642498AG-G-83630HCID 178418339Butyllithium

생성물 1

HCID 692238282-((3S,5R)-3,5-Dimethyl-cyclohexylidene)-[1,3]dithiane수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-trimethylsilyl-1,3-dithiane (30.1 g, 0.16 mol) in THF (250 mL) at 0° C. under an argon atmosphere was added a solution of n-butyl lithium (2.5 M in hexanes, 64 mL, 0.16 mol) and the mixture was cooled to −78° C. A solution of cis-3,5-dimethyl cyclohexanone (10 g, 0.079 mol) in THF (30 mL) was added over 10 min. After 3.5 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL). The aqueous phase was extracted with EtOAc (100 mL×4) and the combined organic layers were dried (MgSO4) and were evaporated. The reaction by-products were removed by vacuum distillation to yield the desired product (16.6 g, 92%). MH+229

후처리

  1. customAfter 3.5 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL)
  2. extractionThe aqueous phase was extracted with EtOAc (100 mL×4)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. customwere evaporated
  5. customThe reaction by-products were removed by vacuum distillation

출처 및 근거

ORD 기록
ord-43478b8b990d4b0d97a83e09af221f91
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332485B2

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