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Diethyl Ether → 3-(3-{[Tert butyl(dimethyl)silyl]oxy}propyl)-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde

HRID 590411
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HRID 590411 반응식
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[O:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCOCC>CN(C=O)C>[Si:24]([O:23][CH2:22][CH2:21][CH2:20][N:6]1[C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[O:3][C:2]1=[O:1])([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:26])[CH3:25]
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참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 3914742-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde2회HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

생성물 1

HCID 1317344803-(3-{[Tert butyl(dimethyl)silyl]oxy}propyl)-2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde수율 89.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

To a solution of 2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde (Intermediate 7, 300 mg, 1.84 mmol) in DMF (10 mL) were added potassium carbonate (633 mg, 4.58 mmol) and (3-bromopropoxy)(tert-butyl)dimethylsilane (0.47 mL, 2.03 mmol), and the resulting mixture was heated to 75° C. Upon complete disappearance of starting material (ca 16 hours), the solvent was removed under reduced pressure and the solid residue was treated with CH2Cl2 and stirred for 5 min. The suspension was filtered through Celite® and the solid residue washed with additional CH2Cl2. The filtrate was concentrated to dryness and the crude was purified by column chromatography over silica gel, eluting with Hexane:Et2O (from 0 to 32% of Et2O) to give the title compound as a white solid (550 mg, 89% yield).

후처리

  1. customUpon complete disappearance of starting material (ca 16 hours), the solvent was removed under reduced pressure
  2. additionthe solid residue was treated with CH2Cl2
  3. filtrationThe suspension was filtered through Celite®
  4. washthe solid residue washed with additional CH2Cl2
  5. concentrationThe filtrate was concentrated to dryness
  6. customthe crude was purified by column chromatography over silica gel
  7. washeluting with Hexane

출처 및 근거

ORD 기록
ord-b7aa7d0fd18244f1bc4bc678824c5f11
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09233108B2

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