Cyclobutylcarbinol → Methyl 3-(4-chlorophenyl)-2-cyclobutylmethoxypropanoate

HRID 133450

반응식

HRID 133450 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4](=[N+]=[N-])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[CH:16]1([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17]1>C1C=CC=CC=1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([O:21][CH2:20][CH:16]2[CH2:19][CH2:18][CH2:17]2)[C:3]([O:2][CH3:1])=[O:15])=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 78130CyclobutylcarbinolHCID 73879458Methyl 2-diazo-3-(4-chlorophenyl)propanoate

생성물 1

HCID 22270441Methyl 3-(4-chlorophenyl)-2-cyclobutylmethoxypropanoate

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
90 °C

실험 절차

To a solution of 500 mg (2.23 mmol) of methyl-2-diazo-3-(4-chlorophenyl)propanoate (obtained from Step A) and 1.05 mL (5 eq; 11.1 mmol) of cyclobutanemethanol in 5 mL benzene in a pressure tube was added 10 mg (1 mole %) of Rh2(OAc)4 catalyst. The tube was sealed and heated to 90° C. for 1.5 h. The solvents were evaporated under reduced pressure and the crude material was taken up in CH2Cl2 and purified by flash chromatography via gradient elution using mixtures of hexane and EtOAc (100:1 to 50:1). This provided the title compound as a clear oil. TLC Rf=0.53 (4:1 hexanes:EtOAc). 500 MHz 1H NMR (CDCl3): δ 1.68 (m, 2H); 1.85 (m, 1H); 1.88 (m, 1H); 2.01 (m, 2H); 2.53 (sep, 1H); 2.98 (m, 2H); 3.24 (dd, 1H); 3.58 (dd, 1H); 3.76 (s, 3H); 3.98 (dd, 1H); 7.20 (d, 2H); 7.28 (d, 2H).

후처리

  1. customThe tube was sealed
  2. customThe solvents were evaporated under reduced pressure
  3. custompurified by flash chromatography via gradient elution

출처 및 근거

ORD 기록
ord-3e7bf8543f6a4dd487f5a453cadb89a9
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390835B2

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