反応 #74255

反応方程式

HCl

1,8-diazabicyclo[5.4.0]undec-7-ene

methyl 2-bromocyclooctene-3-glycolate

methyl 2-bromocyclooct-1-en-3-glycolate

DBU

→

cyclooct-1-yn-3-glycolic acid

収率 55.0%

溶媒

DMSO

反応条件

後処理

1. 1
   workup.STIRRINGthe combined mixture is stirred overnight at 60° C
2. 2
   抽出extracted with AcOEt
3. 3
   ろ過The organic phase is filtered through a separating
4. 4
   ろ過filter
5. 5
   濃縮is concentrated under vacuum
6. 6
   その他The cyclooct-1-yn-3-glycolic acid 18 is purified on a preparative plate (CH2Cl2/MeOH 9/1)
7. 7
   その他is obtained with a yield of 55% (w=50 mg)

実験手順

150 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 1 mmol) are added to a solution of methyl 2-bromocyclooctene-3-glycolate 17 (0.5 mmol) in anhydrous DMSO at 60° C. After stirring for 15 min, an additional 600 μl of DBU (4 mmol) are added and then the combined mixture is stirred overnight at 60° C. The mixture is acidified with 1M HCl and extracted with AcOEt. The organic phase is filtered through a separating filter and is concentrated under vacuum. The cyclooct-1-yn-3-glycolic acid 18 is purified on a preparative plate (CH2Cl2/MeOH 9/1) and is obtained with a yield of 55% (w=50 mg).

出典