Potassium Carbonate → HCID 86679744, 화합물

HRID 77457노트

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HRID 77457 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][Si:19]([CH2:22][CH2:23][O:24][CH2:25]Cl)([CH3:21])[CH3:20]>CN(C=O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH2:25][O:24][CH2:23][CH2:22][Si:19]([CH3:21])([CH3:20])[CH3:18])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1571672(3H)-Benzoxazolone, 6-hydroxy-HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

생성물 1

HCID 86679744HCID 86679744, 화합물수율 21.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-hydroxybenzo[d]oxazol-2(3H)-one (3 g, 19.85 mmol) in dry DMF (30 mL), K2CO3 (5.54 g, 40.1 mmol) and SEM-Cl (4.79 mL, 27.0 mmol) were added. The reaction mixture was stirred at room temperature for 18 h. Solvent was removed under vacuum. The residue was dissolved in ethyl acetate, washed with water and brine, and dried over sodium sulfate. The organic layer was concentrated under vacuum and the crude product was purified by flash chromatography on silica gel using 10 to 50% ethyl acetate in hexane to give 6-hydroxy-3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]oxazol-2(3H)-one as an white solid (1.2 g, 21%). 1HNMR 400 MHz, DMSO-d6: δ ppm −0.055 (s, 9H), 0.86 (t, J=8.00 Hz, 2H), 3.58 (t, J=8.00 Hz, 2H), 5.19 (s, 2H), 6.64 (dd, J=2.40, 8.40 Hz, 1H), 6.78 (d, J=2.00 Hz, 1H), 7.10 (d, J=8.40 Hz, 1H), 9.52 (s, 1H). LCMS: R.T. 1.845 min; 280.1 [M−H].

후처리

  1. customSolvent was removed under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic layer was concentrated under vacuum
  6. customthe crude product was purified by flash chromatography on silica gel using 10 to 50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-0a0bcbf7771a4576b96448fa275c3cf9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841301B2

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