Imidazole → 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)isobenzofuran-1(3H)-one

HRID 627800노트

반응식

HRID 627800 반응식
[OH:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[O:5]1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>C1COCC1>[Si:18]([O:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[O:5]1)([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 222749702-(3-Phthalidyl)ethanol

생성물 1

HCID 711436383-(2-((tert-butyldimethylsilyl)oxy)ethyl)isobenzofuran-1(3H)-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-(2-hydroxyethyl)-3H-isobenzofuran-1-one (1.03 g, 5.781 mmol) dissolved in THF (10 mL) under N2 and TBDMSCl (958.4 mg, 6.359 mmol) then imidazole (472.3 mg, 6.937 mmol) added at RT. Reaction mixture stirred overnight then concentrated. Residue partitioned between EtOAc and water. Aqueous phase extracted with EtOAc and combined organics dried and concentrated. Residue purified by chromatography (silica, 0-100% EtOAc-petrol gradient elution). Title compound obtained as a colourless oil (1.47 g, 87%), 1H NMR (400 MHz, DMSO) 0.00 (3H, s), 0.01 (3H, s), 0.83 (9H, s), 1.76-1.85 (1H, m), 2.23-2.31 (1H, s), 3.71-3.80 (2H, m), 5.66 (1H, dd), 7.57 (1H, t), 7.68 (1H, d), 7.75 (1H, dt), 7.81 (1H, d); MS (ES+) 293.0.

후처리

  1. customReaction mixture
  2. concentrationthen concentrated
  3. customResidue partitioned between EtOAc and water
  4. extractionAqueous phase extracted with EtOAc
  5. customcombined organics dried
  6. concentrationconcentrated
  7. customResidue purified by chromatography (silica, 0-100% EtOAc-petrol gradient elution)

출처 및 근거

ORD 기록
ord-748b3887af1240b0b088b7c3bbc86a51
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309250B2

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