تفاعل #424411

معادلة التفاعل

benzyl carbonyl chloride

sodium bicarbonate

Sodium bicarbonate

(4-amino-phenyl)-methanol

THF

→

title compound

المردود 57.4%

(4-Hydroxymethyl-phenyl)-carbamic acid benzyl ester

المردود 57.4%

المذيبات

DCM

H2O

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed sequentially with HCl (1M solution, 10 ml)
2. 2
   أخرىThe organic layer was separated
3. 3
   تجفيفdried (MgSO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe resulting residue was purified by flash column chromatography (elution: 50% EtOAc, 50% heptane)

الإجراء التجريبي

Sodium bicarbonate (1.0 g, 12.2 mmol) was added portion-wise to a stirred solution of (4-amino-phenyl)-methanol (0.5 g, 4.06 mmol) in a 1:1 mixture of THF:H2O (16 ml) and the mixture was stirred at room temperature for 5 minutes. After this time, benzyl carbonyl chloride (0.69 g, 4.06 mmol) was added dropwise, followed by a further portion of sodium bicarbonate (0.5 g, 6.1 mmol) and stirring was continued for 1 hour. The reaction mixture was then diluted with DCM (50 ml) and washed sequentially with HCl (1M solution, 10 ml) then NaOH (1M solution, 10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 50% EtOAc, 50% heptane) to give the title compound (0.6 g, 57% yield) as an off-white solid. δH (500 MHz, DMSO) 9.63 (s, 1 H) 7.01-7.39 (m, 9 H) 4.90-5.11 (m, 3 H) 4.30 (d, J=5.63 Hz, 2 H).

المصدر