Reaktion #984069

Reaktionsgleichung

compound

methyl 4-(benzyloxy)-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate

K2CO3

9-BBN

2-methyl-1-propene

→

title compound

Ausbeute 31.0%

methyl 4-(benzyloxy)-2-isobutylbenzoate

Ausbeute 31.0%

Lösungsmittel

DMF

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was transferred via a syringe to a degassed solution
2. 2
   TemperaturThe resulting mixture was heated at 60° C. overnight
3. 3
   SonstigeAfter removal of solvent
4. 4
   Sonstigethe residue was purified by chromatography

Vorschrift

To a condensed liquid 2-methyl-1-propene in THF (10 mL) at −78° C. was added 0.5 M 9-BBN (3 mL, 1.5 mmol), the mixture was allowed to warm up to room temperature with stirring. The mixture was transferred via a syringe to a degassed solution containing the compound of Example 206 (0.5 g, 1.3 mmol), Pd(dppf)Cl2 (82 mg, 0.1 mmol), K2CO3 (0.23 g, 1.7 mmol), water (2 mL) in DMF (21 mL). The resulting mixture was heated at 60° C. overnight. After removal of solvent, the residue was purified by chromatography to afford the title compound (0.11 g, 31% yield). 1HNMR Chloroform-d δ 0.85 (d, 6H), 1.75-1.80 (m, 1H), 2.88 (d, 2H), 3.78 (s, 3H), 5.13 (s, 2H), 6.71-6.80 (m, 2H), 7.30-7.41 (m, 5H), 7.90 (d, 1H). Rf=0.65 ethyl acetate/hexane (1/9).

Quelle