Tetrahydrofuran → 2-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanol

HRID 488562

반응식

HRID 488562 반응식
[C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[C:18]1([CH2:19][CH:20]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8][CH2:9][CH2:10][CH2:11][S:12]2)[OH:21])[CH:22]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

4

반응물 3

HCID 8028Tetrahydrofuran3회HCID 215472-Phenyl-1,3-dithianeHCID 178418339Butyllithium

생성물 1

HCID 222719962-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanol수율 71%

반응 조건

온도
-30 °C

실험 절차

To a solution of 2-phenyl-[1,3]-dithiane (65) (4.0 g, 20.4 mmol) in THF at −30° C. was added a 1.6 M solution of n-butyllithium in THF (15.3 mL, 24.4 mmol). After stirring for 30 minutes at −30° C., a solution of phenylacetylaldehyde (2.45 g, 20.4 mmol) in tetrahydrofuran was added dropwise at −30° C. The resulting reaction mixture was stirred for another hour at 0° C. The reaction was quenched with saturated NH4Cl solution and extracted with ethyl acetate. The combined organic extracts were washed with saturated NH4Cl solution, brine and dried over Na2SO4. After filtrating and concentrating, the crude product was purified by flash chromatography on silica gel, (25% ethyl acetate in hexanes), to afford 2.63 g (71%) of the title compound (66). 1H NMR (CDCl3, 400 MHz): δ 1.97 (m, 2H), 2.23 (dd, J=4.0, 1.2 Hz, 1H), 2.43 (dd, J=13.6, 10.2 Hz, 1H), 2.77 (m, 4H), 3.02 (d, J=13.6 Hz, 1H), 4.07 (m, 1H), 7.44-7.13 (m, 8H), 8.02 (dd, J=8.4, 1.4 Hz, 2H).

후처리

  1. customThe resulting reaction mixture
  2. stirringwas stirred for another hour at 0° C
  3. customThe reaction was quenched with saturated NH4Cl solution
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with saturated NH4Cl solution, brine
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtrating
  8. concentrationconcentrating
  9. customthe crude product was purified by flash chromatography on silica gel, (25% ethyl acetate in hexanes),

출처 및 근거

ORD 기록
ord-4af3009cbae14543a6769b28f3b7dfd5
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972341B2

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