Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-{3-[2,2-Bis(hydroxymethyl)ethyl]benzyl}-5-methyl-2-phenyloxazole

HRID 857219Notes

Reaction equation

HRID 857219 reaction equation
CC1(C)[O:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]3[N:17]=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:19][C:20]=3[CH3:21])[CH:10]=2)[CH2:4][O:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:7][CH2:6][CH:5]([CH2:4][OH:3])[CH2:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:19][C:20]=1[CH3:21]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 218667752,2-Dimethyl-5-{3-[(5-methyl-2-phenyloxazol-4-yl)methyl]benzyl}-1,3-dioxane

Product 1

HCID 218666464-{3-[2,2-Bis(hydroxymethyl)ethyl]benzyl}-5-methyl-2-phenyloxazoleYield 106.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture solution of 320 mg of 2,2-dimethyl-5-{3-[(5-methyl-2-phenyloxazol-4-yl)methyl]benzyl}-1,3-dioxane, 21 ml of ethanol and 21 mg of pyridinium p-toluenesulfonate (PPTS) was stirred for 2 hours at 55-60° C. The reaction solution was concentrated and the residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform) to provide 305 mg of the objective compound as colorless oil.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform)

Sources & evidence

ORD record
ord-d2af3bca35134d0094320bb0870666f4
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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