Benzyl Chloride → Ethyl 2-benzyl-1,3-dithiane-2-carboxylate

HRID 1379350

반응식

HRID 1379350 반응식
[CH2:1]([O:3][C:4]([CH:6]1[S:11][CH2:10][CH2:9][CH2:8][S:7]1)=[O:5])[CH3:2].C([Li])CCC.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[CH2:17]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][CH2:8][CH2:9][CH2:10][S:11]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 7503Benzyl ChlorideHCID 88552Ethyl 1,3-dithiane-2-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 303709Ethyl 2-benzyl-1,3-dithiane-2-carboxylate수율 88.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-25 °C

실험 절차

A solution of 3.0 g (15.6 mmol) of 2-ethoxycarbonyl-1,3-dithiane in 40 ml of dry tetrahydrofuran was cooled under inert atmosphere to -78° C. and treated with 7.5 ml (15.6 mmol) of n-butyllithium. The resulting solution was warmed to -25° C., stirred for 20 min, recooled to -78° C., treated with 1.8 ml (15.6 mmol) of benzyl chloride, and stirred at ambient temperature for 16 h. After quenching with aqueous ammonium chloride, the mixture was extracted with ether, washed sequentially with water, aqueous sodium thiosulfate, and brine, dried over MgSO4, and concentrated in vacuo. Flash chromatography using 5% ethyl acetate in hexane gave 3.9 g (88%) of the desired compound. 1H NMR (CDCl3) δ 1.33 (t, J=7 Hz, 3H), 1.85 (qt, J=14, 3 Hz, 1H), 2.11 (dm, J=14 Hz, 1H), 2.69 (dt, J=14, 4 Hz, 2 H), 3.23 (ddd, J=14, 12, 3 Hz, 2H), 3.38 (s, 2H), 4.27 (q, J=7 Hz, 2H), 7.25-7.35 (m, 5H). Mass spectrum (M+NH4)+ =300.

후처리

  1. customrecooled to -78° C.
  2. stirringstirred at ambient temperature for 16 h
  3. customAfter quenching with aqueous ammonium chloride
  4. extractionthe mixture was extracted with ether
  5. washwashed sequentially with water, aqueous sodium thiosulfate, and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-702a12b08c19450ea39ebd6aabd4e4d8
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670675

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