Potassium Hydroxide → Diarachidonyl Methanol

HRID 713856노트

반응식

HRID 713856 반응식
C([O:3][CH:4]([CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34]/[CH:35]=[CH:36]\[CH2:37]/[CH:38]=[CH:39]\[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=O.[OH-].[K+]>CCO>[CH2:5]([CH:4]([CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34]/[CH:35]=[CH:36]\[CH2:37]/[CH:38]=[CH:39]\[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[OH:3])[CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 58559586Diarachidonylmethyl Formate

생성물 1

HCID 58559615Diarachidonyl Methanol수율 107.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The above diarachidonylmethyl formate (III, 0.43 g, 0.71 mmol) and KOH (100 mg) were stirred in 95% EtOH (20 mL) at room temperature under nitrogen overnight. Upon completion of the reaction, most of the solvent was evaporated. The resulting mixture was treated with 20 mL of 2M HCl solution. The aqueous phase was extracted with ether (2×30 mL). The combined ether extract was washed with water (2×25 mL), brine (25 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent gave 0.44 g of IV as pale oil. The crude product was purified by column chromatography on silica gel (230-400 mesh, 40 mL) eluted with 0-5% ethyl acetate gradient in hexanes. This gave 0.41 g of diarachidonyl methanol (IV) as colourless oil.

후처리

  1. customUpon completion of the reaction
  2. custommost of the solvent was evaporated
  3. additionThe resulting mixture was treated with 20 mL of 2M HCl solution
  4. extractionThe aqueous phase was extracted with ether (2×30 mL)
  5. extractionThe combined ether extract
  6. washwas washed with water (2×25 mL), brine (25 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-363655dbf7144157aa238ce67a5bd8f1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186325B2

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