Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 6-Hydroxymethyl-4-(2-triisopropylsilanyloxyethyl)-4H-benzo[1,4]oxazin-3-one

HRID 1712506Notes

Reaction equation

O1CCCCC1[O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15](=[O:18])[N:14]([CH2:19][CH2:20][O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[C:13]=2[CH:32]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15](=[O:18])[N:14]([CH2:19][CH2:20][O:21][Si:22]([CH:23]([CH3:25])[CH3:24])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[C:13]=2[CH:32]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The solution of 7.24 g of 6-(tetrahydropyran-2-yloxymethyl)-4-(2-triisopropylsilanyloxyethyl)-4H-benzo[1,4]oxazin-3-one in 130 ml of ethanol is admixed with 0.392 g of pyridinium p-toluenesulphonate and stirred at 60° C. over 3 hours. The reaction mixture is cooled and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.48 (1:1 EtOAc-heptane); Rt=5.51.

Workup

temperatureThe reaction mixture is cooled
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-9b322e442ecf4836ac4c303d8fe162a2
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790715B2

Reaction notes

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