Ethyl Acetate → 5-(2-Benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester

HRID 560164ノート

反応式

HRID 560164 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]([CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7][CH:6]1O)=[O:4].O=S(Cl)Cl.C1CCN2C(=NCCC2)CC1.CCOC(C)=O>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH2:10][CH:9]([CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:7][CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 235495395-(2-Benzyloxy-ethyl)-2-hydroxy-cyclohexanecarboxylic acid methyl ester

生成物 1

HCID 235495385-(2-Benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 5-(2-benzyloxy-ethyl)-2-hydroxy-cyclohexanecarboxylic acid methyl ester (Intermediate R2, 0.72 g, 2.48 mmol) in pyridine (10 mL) was treated with SOCl2 (0.73 mL, 12.4 mmol) at −20 EC. The mixture was allowed to react for 15 m and was then warmed to 55 EC for 16 h. The solvents were removed under vacuum and the residue was diluted in ether at 0 EC. The solution was quenched with water, washed with 1M HCl, 5% NaOH and brine. The organic material was dried over MgSO4 filtered and freed of solvent. The mixture was diluted with benzene and water was removed by azeotropic distillation under vacuum. The residue was dissolved in benzene (15 mL) and DBU (0.76 mL, 5 mmol) was added. The mixture was reacted for 30 m at rt. After work-up and chromatography on SiO2 with 20% EtOAc:Hx 5-(2-benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester (Intermediate R3) was isolated 0.56 g (82%).

後処理

  1. customto react for 15 m
  2. temperaturewas then warmed to 55 EC for 16 h
  3. customThe solvents were removed under vacuum
  4. additionthe residue was diluted in ether at 0 EC
  5. customThe solution was quenched with water
  6. washwashed with 1M HCl, 5% NaOH and brine
  7. dry with materialThe organic material was dried over MgSO4
  8. filtrationfiltered
  9. additionThe mixture was diluted with benzene and water
  10. customwas removed by azeotropic distillation under vacuum
  11. dissolutionThe residue was dissolved in benzene (15 mL)
  12. customThe mixture was reacted for 30 m at rt

出典と根拠

ORDレコード
ord-cf317c62f23847298abdc726d8ffa8fa
出典データセット
uspto-grants-2011_11
特許番号
US08063086B2

反応ノート

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