Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 5-{[tert-Butyl(diphenyl)silyl]oxy}pent-3-yn-1-ol

HRID 1514335Notes

Reaction equation

HRID 1514335 reaction equation
[C:1]([Si:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][O:12]C1CCCCO1)([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[C:1]([Si:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[O:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][OH:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57829244tert-Butyl-diphenyl-[5-(tetrahydro-pyran-2-yloxy)-pent-2-ynyloxy]-silane

Product 1

HCID 142175645-{[tert-Butyl(diphenyl)silyl]oxy}pent-3-yn-1-olYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 4 (6.12 g, 14.5 mmol) in MeOH (100 mL) was treated with PPTS (0.36 g, 1.43 mmol) at room temperature for overnight. After concentration, the residue was purified by silica gel column chromatography with 20% EtOAc in hexanes to give 3.84 g of product 5 (11.3 mmol, 78%); 1H NMR (CDCl3) δ 7.80˜7.66 (m, 4H), 7.49˜7.35 (m, 6H), 4.33 (t, J=1.9 Hz, 1H), 3.60 (t, J=6.0 Hz, 2H), 2.40 (tt, J=2.2, 6.1 Hz, 2H) 1.05 (s, 9H).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by silica gel column chromatography with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-67e42494df1444e6846dc8af9ccf884c
Source dataset
uspto-grants-2012_07
Patent number
US08222257B2

Reaction notes

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