Diethyl Ether → Diarachidonyl Ketone

HRID 713844

반응식

HRID 713844 반응식
[CH2:1]([CH: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])[OH: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].C(=O)([O-])[O-].[K+].[K+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[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]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 58559615Diarachidonyl MethanolHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 58559565Diarachidonyl Ketone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of diarachidonyl methanol (IV, 0.41 g, 0.71 mmol) and anhydrous potassium carbonate (0.05 g) in 10 mL of CH2Cl2 was added pyridinium chlorochromate (PCC, 0.50 g, 2.3 mmol). The resulting suspension was stirred at room temperature for 90 mins. Ether (50 mL) was then added into the mixture, and the resulting brown suspension was filtered through a pad of floresil (30 mL). The pad was further washed with ether (3×30 mL). The ether filtrate and washes were combined. Evaporation of the solvent gave 0.40 g of an oily residual as a crude product. The crude product was purified by column chromatography on silica gel (230-400 mesh, 10 mL) eluted with 0-3% ether in hexanes. This afforded 0.30 g (75%) of diarachidonyl ketone (V). 1H NMR (400 MHz, CDCl3) δ: 5.3-5.5 (16H, m, 8×CH═CH), 2.82 (12H, t, 6×C═C—CH2—C═C), 2.40 (4H, t, 2×CO—CH2), 2.08 (8H, m, 4× allylic CH2), 1.25-1.65 (20H, m), 0.90 (6H, t, 2×CH3) ppm.

후처리

  1. filtrationthe resulting brown suspension was filtered through a pad of floresil (30 mL)
  2. washThe pad was further washed with ether (3×30 mL)
  3. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-4a0beae47fa4457f8f525168f743ea55
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186325B2

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