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

HRID 627800Notes

Reaction equation

HRID 627800 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-748b3887af1240b0b088b7c3bbc86a51
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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