Diethyl Ether → 2-(7-Hydroxyheptyl)cyclopent-2-en-1-one

HRID 372131

反応式

HRID 372131 の反応式
O1CCCCC1O[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15].O1CCN(C2CCCC=2)CC1.[C:27]1(=[O:32])[CH2:31][CH2:30][CH2:29][CH2:28]1.C(OCC)C>C1C=CC=CC=1>[OH:32][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:8][CH2:9][C:10]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8452CyclopentanoneHCID 702941-MorpholinocyclopenteneHCID 1821847-(Oxan-2-yloxy)heptanal

生成物 1

HCID 205354882-(7-Hydroxyheptyl)cyclopent-2-en-1-one

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
100 °C

実験手順

A mixture of 7-(2-tetrahydropyranyloxy)-heptanal (22 g.) and 1-morpholinocyclopentene, i.e. the morpholine enamine of cyclopentanone, (21.4 g.) in benzene (25 ml.) was heated under reflux for 12 hours under nitrogen, and the water liberated was continuously removed with a Dean and Stark head. Benzene (10 ml.) and then, dropwise, 18% hydrochloric acid (28 ml.) were added and the mixture was stirred for 2 hours. The organic layer was separated and evaporated. Concentrated hydrochloric acid (72 ml.) was added to the residue. The mixture was heated at 100° C. for 1 hour, and then the solution was concentrated to give an oil. Diethyl ether was added, and the ether solution was washed with aqueous sodium bicarbonate and then water, and dried over sodium sulphate. The solvent was evaporated and the residue was distilled under reduced pressure to give 2-(7-hydroxyheptyl)-cyclopent-2-enone (11.7 g.), b.p. 125°-170° C./0.15 mm.Hg, nD25 = 1.490, λmax 228mμ (ethanol).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours under nitrogen
  3. customthe water liberated was continuously removed with a Dean and Stark head
  4. additionBenzene (10 ml.) and then, dropwise, 18% hydrochloric acid (28 ml.) were added
  5. customThe organic layer was separated
  6. customevaporated
  7. additionConcentrated hydrochloric acid (72 ml.) was added to the residue
  8. concentrationthe solution was concentrated
  9. customto give an oil
  10. washthe ether solution was washed with aqueous sodium bicarbonate
  11. dry with materialwater, and dried over sodium sulphate
  12. customThe solvent was evaporated
  13. distillationthe residue was distilled under reduced pressure

出典と根拠

ORDレコード
ord-a2ce3082df4b49d5940bf99105242631
出典データセット
uspto-grants-1978_05
特許番号
US04088821

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