Sodium t-butoxide → HCID 68839471, compound

A solution of the product from Step 4 (0.50 g, 1.24 mmol) in N,N-dimethylformamide (3.0 mL) was cooled to 0° C. and sodium tert-butoxide (0.24 g, 2.54 mol) was added. The reaction was stirred and warmed to room temperature over 1.5 hours. The reaction was quenched by the addition of ice (50 g) and the resulting mixture was diluted with H2O (20 mL), methyl tert-butyl ether (30 mL) and ethyl acetate (100 mL). The organic layer was separated, washed with a 2% lithium chloride solution (20 mL) and then saturated sodium chloride solution (20 mL). The organic layer was dried over sodium sulfate and concentrated to afford a solid that was triturated with a 1:1 cyclohexan/heptane mixture to provide 0.31 g (68%) of the product as a light-yellow solid. 1H NMR (400 MHz, Methanol-d4) δ 7.38-7.18 (m, 5H), 4.87-4.51 (m, 1H), 4.22-4.11 (m, 1H), 3.94-3.48 (m, 4H), 3.59 (s, 3H), 3.22-3.07 (m, 1H), 2.78-2.64 (m, 2H), 2.61-2.43 (m, 2H), 2.40-2.13 (m, 3H). MS 368.2 (AP+, 100).

1. customThe reaction was quenched by the addition of ice (50 g)
2. additionthe resulting mixture was diluted with H2O (20 mL), methyl tert-butyl ether (30 mL) and ethyl acetate (100 mL)
3. customThe organic layer was separated
4. washwashed with a 2% lithium chloride solution (20 mL)
5. dry with materialThe organic layer was dried over sodium sulfate
6. concentrationconcentrated
7. customto afford a solid
8. customthat was triturated with a 1:1 cyclohexan/heptane mixture

ORD record

ord-ffb50126d14943fe8f0aae5fdde7f085

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485641B2