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

HRID 2041512Notes

Reaction equation

HRID 2041512 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-af991d05f34e4d1287a570f37cea0ba9
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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