Dimethyl Sulfoxide → HCID 69769063, 화합물

HRID 1529841노트

반응식

HRID 1529841 반응식
C[O-].[Na+].CS(C)=O.CO[C:10](=[O:24])[CH2:11][CH2:12][C:13]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[O:14]>C1(C)C=CC=CC=1>[CH3:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][CH2:16][CH:15]1[C:10](=[O:24])[CH2:11][CH2:12][C:13]1=[O:14]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 10942334Sodium Methoxide2회HCID 86601513HCID 86601513, 화합물

생성물 1

HCID 69769063HCID 69769063, 화합물수율 82.5%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

In a 5 L 3-neck round bottom flask fitted with mechanical stirrer, a distillation system, a 2 L dropping funnel, and an argon inlet, was poured sodium methoxide solution (25 wt. % solution in methanol, 200 mL). Toluene (1.0 L) was added and methanol was removed off by distillation with an heating mantle. To the sodium methoxide suspension, methyl sulfoxide (13.4 mL, 0.4 eq) was added and a solution of 44 (121.0 g, 0.46 mol) in toluene (2.0 L) was slowly added over a period of 2 h. The distillation was continued during the addition and additional 30 minutes (until 0.5 L residual toluene). The reaction mixture was cooled and water (1 L) was added. Toluene was extracted and thrown away. The aqueous phase was acidified with 10% HCl until pH 1 and extracted with dichloromethane (4×800 mL). The combined organic phase was washed with brine, dried over magnesium sulfate, and rotary evaporated to give the cyclopentanedione 45 (81.3 g, 75%) as a brown heavy oil. 1H NMR (400 MHz, CD3OD) δ 2.42 (t, J=7.1 Hz, 2H), 2.51 (s, 4H), 3.38 (s, 3H), 3.55-3.61 (m, 4H), 3.67 (m, 2H), 4.68 (s, 2H) ppm.

후처리

  1. customIn a 5 L 3-neck round bottom flask fitted with mechanical stirrer
  2. custommethanol was removed off by distillation with an heating mantle
  3. distillationThe distillation
  4. additionwas continued during the addition and additional 30 minutes (until 0.5 L residual toluene)
  5. temperatureThe reaction mixture was cooled
  6. additionwater (1 L) was added
  7. extractionToluene was extracted
  8. extractionextracted with dichloromethane (4×800 mL)
  9. washThe combined organic phase was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. customrotary evaporated

출처 및 근거

ORD 기록
ord-1b9ed78539d044f9afa6777d498682e6
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090651B2

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