Water → 2-Cyclohexene 1,3-cyclopentanedione

HRID 397465

반응식

HRID 397465 반응식
O[Li].[OH2:3].Br[CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]=[CH:6]1.[OH2:11]>>[CH2:10]1[CH2:9][CH2:8][CH2:7][CH:6]=[CH:5]1.[C:9]1(=[O:11])[CH2:8][CH2:7][C:5](=[O:3])[CH2:10]1

참가 물질

4

반응물 3

HCID 962WaterHCID 1370573-BromocyclohexeneHCID 168937Lithium hydroxide, monohydrate2회

생성물 1

HCID 693755332-Cyclohexene 1,3-cyclopentanedione

실험 절차

To a suspension of 1,3-cyclopentandedione (4.00 g, 0.040 mmol) in water (30 ml) were added LiOH.H2O (1.88 g, 0.045 moll) and 3-bromocyclohexene (7.18 g, 0.045 mmol). The solution was stirred overnight, the pH raised to 12-14 (LiOH.H2O) and stirred for 2 h. The solution was washed with Et2O (4×40 ml), acidified to pH 1-2 and resulting solids isolated by filtration, washed and dried to give 2-cyclohexene-1,3-cyclopentanedione. [δH (CD3OD) 5.69 (1H, m), 5.44 (1H, m), 3.20 (1H, m), 2.47 (4H, s), 2.15-1.19 ˜(6H, m). m/z ESI, 70V) 179 (MH+)]. The product was dissolved in EtOH (50 ml) and reduced under an atmosphere of H2 at RT with Pd/C (200 mg). After 5 h the reaction was filtered and the solvent removed to give the title compound as a white solid (890 mg 12%). δH (CD3OD) 2.44 (4H, 2), 2.39 (1H, m), 1.85-1.70 (5H, m), 1.50-1.45 (2H, m), 1.35-1.15 (3H, m). m/z (ESI, 70V) 181 (MH+).

후처리

  1. stirringstirred for 2 h
  2. washThe solution was washed with Et2O (4×40 ml)
  3. customresulting solids
  4. customisolated by filtration
  5. washwashed
  6. customdried

출처 및 근거

ORD 기록
ord-ecfc3e6ccba74a959a777080e86800c8
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610700B2

연결된 노트

불러오는 중…