Hydrochloric Acid → 8-Hydroxy-5-eicosynoic acid

HRID 1165247

반응식

HRID 1165247 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 147482558-Hydroxy-5-eicosynoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
0 °C

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-f371309d0a33471a9f576cbf56a49a39
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04908384

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