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

HRID 133165노트

반응식

HRID 133165 반응식
[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]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 235495395-(2-Benzyloxy-ethyl)-2-hydroxy-cyclohexanecarboxylic acid methyl ester2회

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
55 °C

실험 절차

A solution of 5-(2-benzyloxy-ethyl)-2-hydroxy-cyclohexanecarboxylic acid methyl ester (Intermediate A2) (0.72 g, 2.48 mmol) in pyridine (10 mL) was treated with SOCl2 (0.73 mL, 12.4 mmol) (available from Aldrich) at −20° C. The mixture was allowed to react for 15 m and was then warmed to 55° C. for 16 h. The solvents were removed under vacuum and the residue was diluted in ether at 0° C. 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 A3) was isolated 0.56 g (82%).

후처리

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

출처 및 근거

ORD 기록
ord-47a3327ebee84ec8b4e9a3ed361841e8
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390829B2

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