Oxalyl chloride → 4-Benzyloxy-2-fluorobutyronitrile

HRID 568963Notes

Reaction equation

HRID 568963 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][CH2:15][CH2:16][CH:17]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C[Si]([C:23]#[N:24])(C)C.C(N(S(F)(F)[F:31])CC)C>[I-].[Zn+2].[I-]>[CH2:7]([O:14][CH2:15][CH2:16][CH:17]([F:31])[C:23]#[N:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 82115Trimethylsilyl cyanideHCID 123472(Diethylamino)sulfur trifluorideHCID 108882613-(Benzyloxy)propanal

Product 1

HCID 201494584-Benzyloxy-2-fluorobutyronitrile

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

The compound 1,3-propanediol 13 is mono-alkylated to yield the 3-benzyloxy-1-propanol, which is then oxidized by means of oxalyl chloride to the corresponding 3-benzyloxy-1-propanal, 15. Reaction with trimethylsilylcyanide, preferably in the presence of a catalytic amount of zinc iodide, followed by treatment with diethylaminosulfurtrifluoride results in the formation of 4-benzyloxy-2-fluorobutyronitrile, 16.

Sources & evidence

ORD record
ord-b6de60400abe4129a15e14c9378f3cba
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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