1,2-Dichloroethane → HCID 58629819, compound

To a stirred solution of 2-(trimethylsilyl) ethanol (0.56 mL, 3.91 mmol) in THF (1 mL) at rt under nitrogen, was added 4-DMAP (113 mg, 0.92 mmol) followed by EDC (177 mg, 0.92 mmol). After about 1 minute Et3N (170 μL, 1.22 mmol) was added, drop-wise followed by 4-(4-hydroxyphenyl)butanoic acid (150 mg, 0.83 mmol) in THF (4 mL) and the mixture stirred at rt for 18 hours. The mixture was then partitioned between Et2O (25 mL) and aqueous HCl (2M, 30 mL) and the layers separated. The aqueous layer was re-extracted with Et2O (20 mL) and the combined organic layer washed with brine (50 mL), dried (MgSO4) and concentrated under vacuum to give a ‘chalk-white’ milky oil. Purification by SPE (silica, 5 g Cartridge) eluting with cyclohexane:EtOAc (gradient 25:1 to 1:2) afforded the title compound (55 mg).

1. customThe mixture was then partitioned between Et2O (25 mL) and aqueous HCl (2M, 30 mL)
2. customthe layers separated
3. extractionThe aqueous layer was re-extracted with Et2O (20 mL)
4. washthe combined organic layer washed with brine (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under vacuum
7. customto give a ‘chalk-white’ milky oil
8. customPurification by SPE (silica, 5 g Cartridge)
9. washeluting with cyclohexane

ORD record

ord-1e876992b8c74ee6b193f1ad13c099b7

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07338960B2