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Hexanoic--d5 Acid synthesis

2synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 4 steps
1: 98 percent / imidazole / 12 h / 25 °C
2: 1.) n-BuLi, 2.) D2O / 1.) THF, hexane, -78 deg C, 45 min, 2.) from -78 deg C to RT, 1 h
3: 100 percent / D2 (99.5percent) / Rh on alumina / tetrahydrofuran / 12 h / 25 °C
4: 88 percent / Jones reagent / acetone / 0 °C

References:

Marron, B.E.;Spanevello, R.A.;Elisseou, M.E.;Serhan, C.N.;Nicolaou, K.C. [Journal of Organic Chemistry,1989,vol. 54,# 23,p. 5522 - 5527]