Tetrahydro-4H-pyran-4-ol → HCID 55139138, compound

HRID 911648Notes

Reaction equation

HRID 911648 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1.Br[CH2:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1>C1COCC1>[O:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 74956Tetrahydro-4H-pyran-4-olHCID 869964-(Bromomethyl)benzonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 55139138HCID 55139138, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add sodium bis(trimethylsilyl)amide (2.8 mL, 5.61 mmol, 2M solution in THF) to a solution of tetrahydro-pyran-4-ol (572 mg, 5.61 mmol) in anhydrous THF (20 mL) and stir for 30 min. Add a solution of 4-bromomethyl-benzonitrile (1 g, 5.1 mmol) in anhydrous THF (5 mL) and stir the resulting mixture overnight at room temperature. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with cyclohexane/EtOAc (98:2 to 1:1 gradient) to obtain the desired intermediate as a white solid (845 mg, 76%). GC-MS m/z: 217 (M+);

Workup

  1. stirringstir the resulting mixture overnight at room temperature
  2. concentrationConcentrate in vacuo
  3. custompurify the crude mixture by chromatography on silica gel eluting with cyclohexane/EtOAc (98:2 to 1:1 gradient)

Sources & evidence

ORD record
ord-51bf39ec1bff462a8d87678dd975b51f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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