4-Nitrophenol → 4-Nitrophenyl 4-(4,4'-dimethoxytrityloxy)butyrate

HRID 1723609Notes

Reaction equation

[Na].[OH:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH3:9][O:10][C:11]1[CH:32]=[CH:31][C:14]([C:15](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1.[N+:33]([C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=1)([O-:35])=[O:34].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH3:9][O:10][C:11]1[CH:32]=[CH:31][C:14]([C:15]([O:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][C:39]2[CH:40]=[CH:41][C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=2)=[O:7])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 22 °C

Procedure

The sodium salt of 4-hydroxybutyric acid (1.26 g; 10 mmol) is dissolved in anhydrous pyridine (30 ml), and 4,4′-dimethoxytrityl chloride (3.39 g; 3.05 mmol) is added. After 16 hours, 4-nitrophenol (1.39 g; 10 mmol) and N,N′-dicyclohexylcarbodiimide (2.06 g; 10 mmol) are added, and the mixture is stirred at 22° C. for a further 48 hours. The precipitated dicyclohexylurea is filtered off and washed with dichloromethane. The filtrate is concentrated and the resulting residue is coevaporated twice with toluene. The residue is purified on a silica gel column (10-50% ethyl acetate and 1% triethylamine in petroleum ether). The desired compound is obtained in the form of a pale yellowish-colored oil.

Workup

filtrationThe precipitated dicyclohexylurea is filtered off
washwashed with dichloromethane
concentrationThe filtrate is concentrated
customThe residue is purified on a silica gel column (10-50% ethyl acetate and 1% triethylamine in petroleum ether)

Sources & evidence

ORD record: ord-f53083cc4a4d49238dacc84eedf1a2d3
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485421B2

Reaction notes

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