Dichloromethane → 3-[(Tetrahydro-pyran-2-yloxy)-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

HRID 1161025Notes

Reaction equation

HRID 1161025 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(=O)([O-])O.[Na+]>[O:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[O:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:20]([CH3:21])[CH3:22])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 666996123-[Hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

Product 1

HCID 574382963-[(Tetrahydro-pyran-2-yloxy)-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrileYield 100.4%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Stir a solution of 3-[hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile (12 g, 30.3 mmol), 3,4-dihydro-2H-pyran (3.6 mL, 39.4 mmol) and dichloromethane (250 mL) at room temperature. Add pyridinium p-toluenesulfonate (0.8 g, 3.03 mmol) and stir the resulting mixture 18 hours at room temperature. Dilute the reaction mixture with aqueous saturated sodium hydrogen carbonate (100 mL) and separate the layers. Extract the aqueous layer is washed with dichloromethane (2×50 mL), combine the organic layers, dry with magnesium sulfate, filter and concentrate. Purify the residue via silica chromatography eluting with hexanes to 8:2 hexanes:ethyl acetate to afford the title compound (14.6 g, 100%) as a colorless oil. LCMS (m/z) 478 M−1.

Workup

  1. customseparate the layers
  2. extractionExtract the aqueous layer
  3. washis washed with dichloromethane (2×50 mL)
  4. dry with materialdry with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue via silica chromatography
  8. washeluting with hexanes to 8:2 hexanes

Sources & evidence

ORD record
ord-97c83afb6806483fa0909e585eb6b9a0
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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