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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
ノート
印刷プレビュー

反応式

HRID 590411 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 3914742-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde2 回HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b7aa7d0fd18244f1bc4bc678824c5f11
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09233108B2

反応ノート

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