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

HRID 627800ノート

反応式

HRID 627800 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-748b3887af1240b0b088b7c3bbc86a51
出典データセット
uspto-grants-2016_04
特許番号
US09309250B2

反応ノート

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