p-Toluenesulfonic acid → HCID 67715663, 화합물

HRID 881765노트

반응식

HRID 881765 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:18])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(O)(C1C=CC(C)=CC=1)(=O)=O>CC(C)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:18])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 99957018-(4-Bromophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

생성물 1

HCID 67715663HCID 67715663, 화합물수율 104.5%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

To a mixture of 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (0.99 g, 3.2 mmol) in acetone (10 mL) and water (5 mL) was added Ts-OH (12 mg, 0.063 mmol) and the reaction was let stir in at 75° C. oil bath for 1 hr. The resulting reaction mixture was cooled to rt and the acetone was removed by rotary evaporation in vacuo. The resulting aqueous mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated by rotary evaporation in vacuo to afford 0.9 g of a crude pale yellow solid which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.84-1.98 (m, 2H), 2.06-2.29 (m, 4H), 2.76 (td, J=13.8, 6.3 Hz, 2H), 5.47 (s, 1H), 7.51 (s, 4H). ESI-MS m/z: not ionized [M+H]+, retention time 1.18 min (condition E).

후처리

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to rt
  3. customthe acetone was removed by rotary evaporation in vacuo
  4. extractionThe resulting aqueous mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation in vacuo

출처 및 근거

ORD 기록
ord-722df797125a4cc6858db94dfcbbbea9
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993619B2

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