Tetrahydrofuran → Methyl 2-methyl-4-hydroxybutyrate

Reaction equation

[CH3:1][O:2][C:3](=[O:9])[CH:4]([CH3:8])[CH2:5][C:6]#N.C1C[O:13]CC1.C1CCCCCCCCCCC1.CC1CCOC1=O>O>[CH3:8][CH:4]([CH2:5][CH2:6][OH:13])[C:3]([O:2][CH3:1])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 0.05 mmol RuHCi(H2)(PCy3)2, 0.54 mmol methyl-3-cyanoisobutyrate (prepared by addition of HCN to methyl methacrylate), 17.7 g THF, 15.3 g water, and 0.0596 g cyclododecane (internal standard for gc analysis) was stirred in an autoclave and heated to 100° C. under 7000 kPa H2. After 3.2 hours, the nitrile was completely and cleanly converted to methyl-butyrolactone, which formed by transesterification/cyclization of the intermediate hydroxyester, methyl 2-methyl-4-hydroxybutyrate.