تفاعل #1901379

معادلة التفاعل

sodium bicarbonate

hept-2-yn-1-ol

7-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol

crude acid 29

7-Acetoxy-hept-5-ynoic acid

acetyl chloride

→

7-Hydroxy-hept-5-ynoic acid methyl ester

المردود 92.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   تجفيفThe mixture was dried (MgSO4)
2. 2
   ترشيحfiltered through celite
3. 3
   أخرىevaporated in vacuo
4. 4
   أخرىPurification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes)

الإجراء التجريبي

The crude acid 29 (6.333 g) was treated with a 1% solution of acetyl chloride in methanol (60 mL). After 16 h, sodium bicarbonate (1.966 g, 23.4 mmol) was added. The mixture was dried (MgSO4), filtered through celite and evaporated in vacuo. Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes) gave 7-Hydroxy-hept-5-ynoic acid methyl ester 30 (3.022 g, 19.3 mmol, 92% from 7-tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol 27).

المصدر