2,5-Dimethoxytetrahydrofuran → 1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)pyrrole

HRID 365572Notes

Reaction equation

[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:28])=[C:22]([CH:24]=[CH:25][C:26]=1[Cl:27])[NH2:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([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.CO[CH:31]1[CH2:35][CH2:34][CH:33](OC)O1>C(O)(=O)C>[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:28])=[C:22]([N:23]2[CH:31]=[CH:35][CH:34]=[CH:33]2)[CH:24]=[CH:25][C:26]=1[Cl:27])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichloroaniline (6.08 g) in acetic acid (15 ml) was added 2,5-dimethoxytetrahydrofuran (1.87 g). The mixture was stirred at 90° C. for 1 hour and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluted with n-hexane-ethyl acetate to give 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]pyrrole (5.82 g) as a pale yellow oil.

Workup

customevaporated under reduced pressure
customThe residue was purified by a silica gel column chromatography
washeluted with n-hexane-ethyl acetate

Sources & evidence

ORD record: ord-685bf0d5db6046ee98f64f985031a4fb
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127389

Reaction notes

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