Reacción #160159

Ecuación de reacción

HCl

4-bromobenzoic acid

n-butyllithium

oxetan-3-one

4-(3-hydroxyoxetan-3-yl)benzoic acid benzoic acid

→

4-(3-Hydroxyoxetan-3-yl)benzoic acid

Disolventes

THF

ethyl acetate

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 30 minutes at −78° C.
2. 2
   OtroThe layers were separated
3. 3
   Extracciónthe aqueous was re-extracted with ethyl acetate (15 mL)
4. 4
   LavadoThe combined organics were washed with brine solution (10 mL)
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otroto give a white solid

Procedimiento

To 4-bromobenzoic acid (434 mg, 2.16 mmol) in THF (9 mL) at −78° C. was added dropwise n-butyllithium (2.84 mL of 1.6 M in hexanes, 4.54 mmol). The reaction mixture was stirred for 30 minutes, then oxetan-3-one (218 mg, 3.03 mmol) in THF (1 mL) was added dropwise. The reaction mixture was stirred for 30 minutes at −78° C. and allowed to warm to room temperature over 30 minutes. The reaction mixture was diluted with ethyl acetate (15 mL) and acidified to pH 2 with 2 N HCl. The layers were separated and the aqueous was re-extracted with ethyl acetate (15 mL). The combined organics were washed with brine solution (10 mL), dried over MgSO4 and concentrated in vacuo to give a white solid as a 1:1 mixture of 4-(3-hydroxyoxetan-3-yl)benzoic acid/benzoic acid (380 mg, 91%).

Fuente