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

HRID 30370

Reaction equation

[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

Participants

Conditions

Temperature: 90 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-e39e49b444e34a0e8bb921bb715389dc
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423067B2

Linked notes

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