تفاعل #519292

معادلة التفاعل

compound

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

K2CO3

9-BBN

2-methyl-1-propene

→

title compound

المردود 31.0%

Methyl 4-(benzyloxy)-2-isobutylbenzoate

المردود 31.0%

المذيبات

DMF

water

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was transferred via a syringe to a degassed solution
2. 2
   درجة الحرارةThe resulting mixture was heated at 60° C. overnight
3. 3
   أخرىAfter removal of solvent
4. 4
   أخرىthe residue was purified by chromatography

الإجراء التجريبي

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).

المصدر