Trimethylsilyl cyanide → 4-Benzyloxy-2-fluorobutyronitrile

HRID 568971Notes

Reaction equation

HRID 568971 reaction equation
C[Si]([C:5]#[N:6])(C)C.[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(N(S(F)(F)[F:25])CC)C>C(Cl)Cl>[CH2:7]([O:14][CH2:15][CH2:16][CH:17]([F:25])[C:5]#[N:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

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

Product 1

HCID 201494584-Benzyloxy-2-fluorobutyronitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

Under nitrogen, a mixture of trimethylsilyl cyanide (1.335 mL, 10 mmoles) and 15 (1.64 g, 10 mmoles) is heated at 100° C. for 6 hours. The reaction is monitored by NMR (88% conversion after 6 hours). The mixture is cooled to 5° C. (ice bath), and CH2Cl2 (12 mL) is added, followed by diethylaminosulfurtrifluoride, (0.46 g, 9.1 mmoles), dissolved in CH2Cl2 (8 mL) at about 5° C.

Workup

  1. customis monitored by NMR (88% conversion after 6 hours)
  2. additionis added

Sources & evidence

ORD record
ord-1717436c494c46e3b4f296899bbbec3b
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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