Sodium hydride → HCID 15907745, compound

To a solution of methyl glycolate (10 mL, 130 mmol) in THF (50 mL) at -70° C. (acetone-dry ice) was added in small portions, with stirring 60% NaH in oil (1.6 g, 111 mmol). To the resulting white suspension was added a solution of 3,5-dinitrobenzylchloride (5.0 g, 23 mmol). The reaction was allowed to warm to room temperature and acetic acid (2 mL) was added to quench excess NaH. The reaction mixture was concentrated and the residual tan oil was partitioned between water and CH2Cl2. The organic phase was washed with water and dried over Na2SO4. The crude product obtained after concentration was chromatographed on a silica gel column (4×25 cm) eluting with 33% ethyl acetate in hexane. Concentration of appropriate fractions followed by drying in vacuo gave 5.1 g (93%) of the desired product 2.1 as a pale yellow crystalline solid: 1H NMR (CDCl3) δ 8.98 (s, 1H, C4 --H), 8.59 (s, 2H, C2 --H), 4.85 (s, 2H, CH2), 4.29 (s, 2H, CH2), 3.81 (s, 3H, CH3); 13C NMR (CDCl3) δ 170.16, 148.58, 142.33, 127.30, 118.15, 71.10, 68.07, 52.18.

1. customto quench excess NaH
2. concentrationThe reaction mixture was concentrated
3. customthe residual tan oil was partitioned between water and CH2Cl2
4. washThe organic phase was washed with water
5. dry with materialdried over Na2SO4
6. customThe crude product obtained
7. concentrationafter concentration
8. customwas chromatographed on a silica gel column (4×25 cm)
9. washeluting with 33% ethyl acetate in hexane
10. customby drying in vacuo

ORD record

ord-3166a6a1d3b74305b0a29a4edbe5e63a

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06072046