Potassium Hydroxide → Diarachidonyl Methanol

HRID 713856ノート

反応式

HRID 713856 の反応式
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]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 58559586Diarachidonylmethyl Formate

生成物 1

HCID 58559615Diarachidonyl Methanol収率 107.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-363655dbf7144157aa238ce67a5bd8f1
出典データセット
uspto-grants-2015_11
特許番号
US09186325B2

反応ノート

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