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

HRID 30370

反応式

HRID 30370 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e39e49b444e34a0e8bb921bb715389dc
出典データセット
uspto-grants-2008_09
特許番号
US07423067B2

関連ノート

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