Sodium Chloride → 2,6-Dichloro-4-[3-((tert-butyldimethylsilanyloxy))-2-(tert-butyldimethylsilanyloxymethyl)-propoxy)-benzaldehyde

HRID 1006472노트

반응식

HRID 1006472 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[Si:12]([O:19][CH2:20][CH:21]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:22]OS(C)(=O)=O)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[Na+].[Cl-]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:22][CH:21]([CH2:28][O:29][Si:30]([C:33]([CH3:34])([CH3:36])[CH3:35])([CH3:31])[CH3:32])[CH2:20][O:19][Si:12]([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

참가 물질

8

반응물 5

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 5283822,6-Dichloro-4-hydroxybenzaldehydeHCID 11015147Methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester

생성물 1

HCID 1317245862,6-Dichloro-4-[3-((tert-butyldimethylsilanyloxy))-2-(tert-butyldimethylsilanyloxymethyl)-propoxy)-benzaldehyde

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3.43 g (18 mmol) A1, 7.40 g (18 mmol) methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester (Kim, H. S., et al., J. Med. Chem. 44 (2001) 3092-3108), 3.72 g (27 mmol) potassium carbonate and 41 mg (0.15 mmol) 18-crown-6 were stirred in 40 ml dimethylformamide at 40° C. overnight. 600 ml ethyl acetate and 250 ml aqueous NaCl were added. The organic layer was washed four times with saturated aqueous NaCl (80 ml each), dried over sodium sulfate and evaporated to dryness. Column chromatography of the residue on SiGel (heptane/ethyl acetate 10:1) yielded 508 mg (27%) A26.

후처리

  1. washThe organic layer was washed four times with saturated aqueous NaCl (80 ml each)
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customColumn chromatography of the residue on SiGel (heptane/ethyl acetate 10:1) yielded 508 mg (27%) A26

출처 및 근거

ORD 기록
ord-37be19c42e71443ab924b3311253b6a8
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790852B2

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