Benzyl Salicylate → Benzyl 2-[2,6-Bis(isopropyl)phenoxycarbonyloxy]-benzoate

HRID 2103788

반응식

HRID 2103788 반응식
[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(N(CC)CC)C.[CH:25]([C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:29]=1[O:30][C:31](Cl)=[O:32])([CH3:27])[CH3:26]>ClCCl.CN(C1C=CN=CC=1)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH:25]([C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:29]=1[O:30][C:31]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:32])([CH3:27])[CH3:26]

참가 물질

7

반응물 3

HCID 8363Benzyl SalicylateHCID 8471TriethylamineHCID 2716192,6-Di(propan-2-yl)phenyl carbonochloridate

생성물 1

HCID 21110017Benzyl 2-[2,6-Bis(isopropyl)phenoxycarbonyloxy]-benzoate수율 57%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 311Citric Acid용매HCID 6344Dichloromethane용매2회

실험 절차

To a cooled (0° C.) solution of benzyl salicylate (0.77 g, 3.3 mmol) in dichloromethane (6 mL) was added triethylamine (0.52 mL, 3.7 mmol) and a catalytic amount of DMAP. To this mixture a suspension of compound (104) (0.9 g, 3.7 mmol, crude product from last step) in dichloromethane (4 mL) was further added. The reaction was allowed to warm to room temperature slowly and stirred for 14 h. The reaction mixture was then diluted with 10% aqueous citric acid solution (10 mL) and extracted with ethyl ether (2×40 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified by radial chromatography on silica gel (eluting with ethyl acetate/hexane) to afford 0.8 g (57% yield over two steps) of the title compound (105).

후처리

  1. additionwas further added
  2. extractionextracted with ethyl ether (2×40 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by radial chromatography on silica gel (eluting with ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-274f4251ac5f470e866c915c104f7fc3
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576127B2

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