Hydrochloric Acid → 8-Hydroxy-5-eicosynoic acid

HRID 1165247

反応式

HRID 1165247 の反応式
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[Li]CCCC.CCCCCC.[CH2:20]([CH:32]1[CH2:34][O:33]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].Cl>O.CN(P(N(C)C)(N(C)C)=O)C>[OH:33][CH:32]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:34][C:6]#[C:5][CH2:4][CH2:3][CH2:2][C:1]([OH:8])=[O:7]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 186041,2-EpoxytetradecaneHCID 1430365-Hexynoic acidHCID 178418339Butyllithium

生成物 1

HCID 147482558-Hydroxy-5-eicosynoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
0 °C

実験手順

In a dry flask under argon was placed 10.2 g of 5-hexynoic acid, the product of lb, and 100 ml of HMPA (distilled over NaH). The solution was cooled to 0° C. and a solution of n-BuLi in hexane (115 ml, 0.185 mol) was added dropwise. After stirring for 1 hr., 21.7 g (0.118 mole) of dodecyl oxirane, the product of 1 c, was added dropwise. The reaction mixture was allowed to stir at room temperature for 3 days and then poured into 150 ml of ice and water. The aqueous solution was acidified with 5% HCl and then extracted with ether. The ether solution was washed with H2O, saturated with NaCl solution and then dried over MgSO4. Removal of solvent yielded crude product which was recrystallized in cyclohexane to give the title compound, mp 80.5°-81°.

後処理

  1. customIn a dry flask under argon was placed
  2. stirringto stir at room temperature for 3 days
  3. extractionextracted with ether
  4. washThe ether solution was washed with H2O, saturated with NaCl solution
  5. dry with materialdried over MgSO4
  6. customRemoval of solvent
  7. customyielded crude product which
  8. customwas recrystallized in cyclohexane

出典と根拠

ORDレコード
ord-f371309d0a33471a9f576cbf56a49a39
出典データセット
uspto-grants-1990_03
特許番号
US04908384

関連ノート

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