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(E)-5-CHLORO-1-PENTENEBORONICACIDPIN synthesis

2synthesis methods
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Yield:154820-95-8 85%

Reaction Conditions:

in dichloromethane;byproducts: H2; dropwise addn. of BH3*(CH3)2S (20 mmol) in (CH3)2S to soln. of pinacol (20 mmol) in dry THF; stirring for 1 h (0°C), then warming (25°C); stirring (1 h); addn. of Cl(CH2)3CCH (10 mmol) at 0°C; stirring (7 h, 25°C);; addn. of ether, pouring soln. into separatory funnel contg. satd. aq. NH4Cl; washing org. phase with satd. aq. NH4Cl, drying over MgSO4; evapg. solvent under vac.; flash chromy. of residue (hexane/ether); E/Z ratio 99:1, determined by chromy. (GLC);;

References:

Rozema, Michael J.;Rajagopal, Duddu;Tucker, Charles E.;Knochel, Paul [Journal of Organometallic Chemistry,1992,vol. 438,# 1.2,p. 11 - 27]

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