1,2,4-Butanetriol → 2,2-Diarachidonyl-4-(2-hydroxyethyl)-[1,3]-dioxolane

HRID 713858

반응식

HRID 713858 반응식
[CH2:1]([C:21]([CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:22])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH2:43](O)[CH:44]([OH:48])[CH2:45][CH2:46][OH:47].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:21]1([CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[O:48][CH:44]([CH2:45][CH2:46][OH:47])[CH2:43][O:22]1)[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

참가 물질

5

반응물 3

HCID 183021,2,4-ButanetriolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 58559565HCID 58559565, 화합물

생성물 1

HCID 585596062,2-Diarachidonyl-4-(2-hydroxyethyl)-[1,3]-dioxolane

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of diarachidonyl ketone (V, 0.30 g, 0.52 mmol), 1,2,4-butanetriol (0.25 g, 2.4 mmol) and pyridinium p-toluenesulfonate (20 mg) in 60 mL of toluene was refluxed under argon overnight with a Dean-Stark tube to remove water. The resulting mixture was cooled to room temperature. The organic phase was washed with water (2×30 mL), brine (30 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent resulted in a yellowish oily residual. The crude product was purified by column chromatography on silica gel (230-400 mesh, 40 mL) with 0-2% methanol in dichloromethane as eluent. This afforded 0.29 g (84%) of pure VI as pale oil.

후처리

  1. temperaturewas refluxed under argon overnight with a Dean-Stark tube
  2. customto remove water
  3. washThe organic phase was washed with water (2×30 mL), brine (30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customEvaporation of the solvent
  6. customresulted in a yellowish oily residual
  7. customThe crude product was purified by column chromatography on silica gel (230-400 mesh, 40 mL) with 0-2% methanol in dichloromethane as eluent

출처 및 근거

ORD 기록
ord-3eaff4a2bdf84e73b84fbcb71895f8d6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186325B2

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