Hydrochloric Acid → HCID 21249534、化合物

HRID 1531597ノート

反応式

HRID 1531597 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 131722423HCID 131722423、化合物

生成物 1

HCID 21249534HCID 21249534、化合物収率 17%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-76405a4f8d2d4df7af2ad00c47499039
出典データセット
uspto-grants-2001_03
特許番号
US06200254B1

反応ノート

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