Water → 4,5-Bis(2-benzyloxyacetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

HRID 12940노트

반응식

HRID 12940 반응식
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1.[CH2:22]([O:29][CH2:30][C:31](Cl)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:34]([O:37][CH2:38][CH3:39])(=O)[CH3:35].ClCCl.[OH2:43]>N1C=CC=CC=1>[CH2:22]([O:29][CH2:30][C:31]([O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[O:17][C:35](=[O:43])[CH2:34][O:37][CH2:38][C:39]3[CH:6]=[CH:15][CH:2]=[CH:3][CH:4]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

7

반응물 5

HCID 962WaterHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 10168RheinHCID 177085Benzyloxyacetyl chloride

생성물 1

HCID 114559804,5-Bis(2-benzyloxyacetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

4,5-Dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (3.0 g) was suspended in pyridine (100 ml) and stirred at RT for 30 mins. Benzyloxyacetyl chloride (3.6 g, 5 equiv.) was added, to give a clear reaction mixture which was stirred at RT over the weekend. The reaction mixture was reduced to a smaller volume and quenched with 2M HCl (200 ml), adjusting the pH to pH 2. An orange solid was isolated by filtration. This crude solid was slurried in water (30 ml), followed by ethyl acetate (30 ml) and dichloromethane (30 ml). A yellow solid was isolated by filtration (3.6 g, 61%).

후처리

  1. customto give a clear reaction mixture which
  2. stirringwas stirred at RT over the weekend
  3. customquenched with 2M HCl (200 ml)
  4. customAn orange solid was isolated by filtration
  5. customA yellow solid was isolated by filtration (3.6 g, 61%)

출처 및 근거

ORD 기록
ord-ba0d0475fac4495ead26baa58c66eb98
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728035B2

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