Water → 5-Benzyloxy-2-trityloxymethyl-4-pyridone

HRID 993301Notes

Reaction equation

[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:28][C:29]1[C:30](=[O:37])[CH2:31][C:32]([CH2:35][OH:36])=[N:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:21]([O:28][C:29]1[C:30](=[O:37])[CH2:31][C:32]([CH2:35][O:36][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:33][CH:34]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 95 °C

Procedure

4-Dimethylaminopyridine (17.55 g) and trityl chloride (40.5 g) are added to a solution of 5-benzyloxy-2-hydroxymethyl-4-pyridone (30.2 g) in dry dimethylformamide and the mixture stirred and heated at 95° C. for 2 hours. After cooling the mixture is poured into iced-water (800 mL) and the precipitate collected, washed with water (2×500 mL) and sucked dry. The solid is boiled with methanol (500 mL) and after cooling the solid is collected, washed with methanol (200 mL) and diethyl ether (2×100 mL) and dried at 80° C. to give 5-benzyloxy-2-trityloxymethyl-4-pyridone (26.5 g) as a white solid, m.p. 233-5° C.

Workup

temperatureAfter cooling the mixture
customthe precipitate collected
washwashed with water (2×500 mL)
customsucked dry
temperatureafter cooling the solid
customis collected
washwashed with methanol (200 mL) and diethyl ether (2×100 mL)
customdried at 80° C.

Sources & evidence

ORD record: ord-1d3e67b3924d48dca6434f8bc7546a61
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472412B1

Reaction notes

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