N-Fluorobenzenesulfonimide → Methyl 2-(2-butynyl)-2-fluorodecanoate

HRID 634972Notes

Reaction equation

HRID 634972 reaction equation
[CH2:1]([CH:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:6]([O:8][CH3:9])=[O:7])[C:2]#[C:3][CH3:4].[Li+].CC([N-]C(C)C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:36])(=O)=O)=CC=1>C1COCC1>[CH2:1]([C:5]([F:36])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:6]([O:8][CH3:9])=[O:7])[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 2724682Lithium diisopropylamideHCID 11470455Methyl 2-(2-butynyl)decanoate

Product 1

HCID 11253872Methyl 2-(2-butynyl)-2-fluorodecanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

This ester was again deprotonated with LDA in THF, as described above, and at −78° C. a solution of N-fluoro benzenesulfonimide (1.1 equivalents) in THF was added dropwise. The mixture was allowed to warm to room temperature, quenched with saturated ammonium chloride solution, and worked up as above. Chromatography on silica gel with 5% ethyl acetate in hexane provided methyl 2-(2-butynyl)-2-fluorodecanoate as an oil.

Workup

  1. customat −78° C.
  2. additionwas added dropwise
  3. customquenched with saturated ammonium chloride solution

Sources & evidence

ORD record
ord-9b7ce819f76541a1a8890a09f41f2da1
Source dataset
uspto-grants-2001_02
Patent number
US06184401B2

Reaction notes

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