Réaction #10177

Équation de réaction

β-ethoxyacrylic acid ethyl ester

2-bromobenzyl phenyl sulfone

tricyclohexylphophine

sodium tert-butoxide

potassium dihydrogen phosphate

→

3-benzenesulfonyl-3H-indene-1-carboxylic acid ethyl ester

Rendement 85.0%

Solvants

tetrahydrofuran

methyl tert-butyl ether

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONUpon complete addition the reaction
2. 2
   Températurewas warmed to room temperature
3. 3
   Températureheated to 60° C. for 2 hours
4. 4
   TempératureThe reaction was cooled to room temperature
5. 5
   AutreThe aqueous layer was separated and saturated by addition of solid sodium chloride
6. 6
   Extractionextracted with ethyl acetate (2×50 mL)
7. 7
   AutreThe organic layer was separated
8. 8
   Lavagewashed twice with aqueous saturated sodium chloride (2×30 mL)
9. 9
   Séchagedried over sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated in vacuo

Mode opératoire

A solution of tricyclohexylphophine (46 mg, 0.164 mmol) in tetrahydrofuran (2.5 mL) under nitrogen was charged with palladium (II) acetate (24.5mg, 0.109 mmol). The reaction mixture was stirred for 45 minutes, then cooled to 0° C. and charged with sodium tert-butoxide (270 mg, 2.73 mmol). After 5 minutes a solution of β-ethoxyacrylic acid ethyl ester (158 μL, 1.09 mmol) and 2-bromobenzyl phenyl sulfone (340 mg, 1.09 mmol) in tetrahydrofuran (2.5 mL) was added dropwise over 2 minutes. Upon complete addition the reaction was warmed to room temperature and then heated to 60° C. for 2 hours. The reaction was cooled to room temperature, then diluted with methyl tert-butyl ether (25 mL) and poured into aqueous potassium dihydrogen phosphate (0.25 M, 25 mL), pH=7. The aqueous layer was separated and saturated by addition of solid sodium chloride and extracted with ethyl acetate (2×50 mL). The organic layer was separated and washed twice with aqueous saturated sodium chloride (2×30 mL), dried over sodium sulfate, filtered and concentrated in vacuo affording 3-benzenesulfonyl-3H-indene-1-carboxylic acid ethyl ester as a light orange oil (304 mg, 0.925 mmol, 85%). 1H NMR (400 MHz, CDCl3) δ 7.88–7.86 (m, 1H), 7.75–7.72 (m, 1H), 7.49–7.43 (m, 3H), 7.36–7.32 (m, 2H), 7.27–7.25 (m, 3H), 5.15 (d, 1H, J=2.1), 4.27 (q, 2H, J=7.1), 1.34 (t, 3H, J=7.1); IR (ATR, neat) 1709, 1649, 1463, 1444, 1314, 1271, 1247, 1188, 1133, 1081, 1044, 773, 752, 722, 686, 575, 528.

Source