Cyclopentanethiol → HCID 55027735, compound

HRID 1190952Notes

Reaction equation

HRID 1190952 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:11]1([SH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.Br[CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>C1COCC1>[CH:11]1([S:16][CH2:18][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 15510CyclopentanethiolHCID 869964-(Bromomethyl)benzonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 55027735HCID 55027735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add sodium bis(trimethylsilyl)amide (20 mL, 40 mmol, 2M solution in THF) to a solution of cyclopentanethiol (4.3 mL, 40 mmol) in anhydrous THF (100 mL) and stir at room temperature under nitrogen for 1 h. Add 4-bromomethyl-benzonitrile (7.85 g, 40 mmol) and stir the mixture for 24 h at room temperature. Reduce solvent in vacuo and wash with saturated aqueous NaHCO3. Extract with DCM (50 mL), wash organic phase with brine (50 mL) and dry over MgSO4 to obtain a light yellow oil suitable for use without additional purification. GC-MS m/z: 217 (M+).

Workup

  1. washReduce solvent in vacuo and wash with saturated aqueous NaHCO3
  2. extractionExtract with DCM (50 mL)
  3. washwash organic phase with brine (50 mL)
  4. dry with materialdry over MgSO4
  5. customto obtain a light yellow oil suitable for use
  6. customwithout additional purification

Sources & evidence

ORD record
ord-267b10402f4e40aa9a5a12ce71ea08bd
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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