Hydrochloric Acid → HCID 21249534, 화합물

HRID 1531597노트

반응식

HRID 1531597 반응식
[O:1]=[C:2]1[CH:16](C(OCC)=O)[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1.C(O)C.Cl.C(OCC)C>O>[C:2]1(=[O:1])[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 131722423HCID 131722423, 화합물

생성물 1

HCID 21249534HCID 21249534, 화합물수율 17%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

The crude ethyl 15-oxocyclopentadeca-3E,11E-dienecarboxylate (prepared as described above) was treated with ethanol (10 ml) and 3N aqueous hydrochloric acid (20 ml) and heated to reflux for 20 hours. The solution was cooled and diethyl ether and water were added. The layers were separated and the organic fraction was dried with magnesium sulfate, filtered and evaporated to provide a brown oil which was purified by column chromatography (10% diethyl ether/hexane) to afford cyclopentadeca-4E,12E-dien-1-one (0.50 g, 17% yield from diethyl hexadeca-4E,12E-diene-1,16-dioate). C15H24O (220.36 g/mole). 1HNMR (500 MHz, CDCl3): 1.15 (m, 4H), 1.34 (m, 4H). 1.97 (m, 4H), 2.24 (m, 4H), 2.45 (m, 4H), 5.30 (m, 2H), 5.39 (m, 2H) ppm. 13CNMR (125 MHz, CDCl3): 26.7, 27.4, 28.4, 31.2, 42.8, 129.2, 131.3, 210.4 ppm. IR (νmax(cm−1)): 2990, 2950, 2910, 2850, 1720, 1440, 1400, 1360, 1080, 980, 720. MS (m/z): 220(M+), 177, 163, 149, 135, 121, 109, 95, 81, 67, 55, 41.

후처리

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. temperatureThe solution was cooled
  4. customThe layers were separated
  5. dry with materialthe organic fraction was dried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto provide a brown oil which
  9. customwas purified by column chromatography (10% diethyl ether/hexane)

출처 및 근거

ORD 기록
ord-76405a4f8d2d4df7af2ad00c47499039
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06200254B1

반응 노트

불러오는 중…