p-Toluenesulfonic acid → HCID 67715663、化合物

HRID 881765ノート

反応式

HRID 881765 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 67715663HCID 67715663、化合物収率 104.5%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-722df797125a4cc6858db94dfcbbbea9
出典データセット
uspto-grants-2015_03
特許番号
US08993619B2

反応ノート

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