4-Bromobutyronitrile → HCID 86699858, compound

HRID 1423313Notes

Reaction equation

HRID 1423313 reaction equation
C([Li])CCC.[S:6]1[CH2:10][CH2:9][S:8][CH:7]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Br[CH2:17][CH2:18][CH2:19][C:20]#[N:21]>C1COCC1.C(OCC)C>[C:20]([CH2:19][CH2:18][CH2:17][C:7]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:8][CH2:9][CH2:10][S:6]1)#[N:21]

Participants

6

Reactant 3

HCID 214124-BromobutyronitrileHCID 88551Ethyl 1,3-dithiolane-2-carboxylateHCID 178418339Butyllithium

Product 1

HCID 86699858HCID 86699858, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (6.5 mL, 1.6 M in hexane) was added to a solution of ethyl 1,3-dithiolane-2-carboxylate (1925 mg, 10 mmol) in THF (10 mL) at −78° C. under N2. The reaction mixture was stirred for 30 min at −78° C. and then 4-bromobutanenitrile (1469 mg, 10 mmol) in THE (10 mL) was added. The mixture was warmed to room temperature and stirred for 30 min. It was diluted with diethyl ether and washed with 1 N HCl and H2O, and dried. Evaporation and purification by column chromatography afforded ethyl 2-(3-cyanopropyl)-1,3-dithiolane-2-carboxylate: LCMS tR=1.86 Min (5 min run, UV254nm), Mass calculated for, M+259.0, observed LC/MS m/z 260.0 (M+H).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 30 min
  3. washwashed with 1 N HCl and H2O
  4. customdried
  5. customEvaporation and purification by column chromatography

Sources & evidence

ORD record
ord-c05425881acc4ff38f0e28d121e98e16
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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