Sodium hydride → 4-[2-(4-formylphenoxy)ethyl]phenyl N-(tert-butyl)carbamate

HRID 1595515Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:21]([N:25]=[C:26]=[O:27])([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[C:21]([NH:25][C:26](=[O:27])[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH:15]=[O:16])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

0.5 g (2.1 mmole) 4-[2-(4-hydroxyphenyl)ethoxy]benzaldehyde was dissolved in tetrahydrofuran, cooled to 0° C. and 0.092 g (2.1 mmole) sodium hydride in tetrahydrofuiran was added. The reaction mixture was stirred until gas development ceased, then 0.4 g (4 mmole) tert-butyl isocyanate in tetrahydrofuran was added and the temperature was allowed to rise to room temperature. The reaction was followed by TLC. More 0.4 g (4 mmole) tert-butyl isocyanate was added. After 3 days the reaction was quenched with ice and sodium hydroxide (aq), extracted with dichloromethane, dried and evaporated. Purification by chromatography on silica gel using ethyl acetate:petroleum ether (1:2) as eluent gave 0.6 g (yield 84%) of 4-[2-(4-formylphenoxy)ethyl]phenyl N-(tert-butyl)carbamate.

Workup

customto rise to room temperature
customAfter 3 days the reaction was quenched with ice and sodium hydroxide (aq)
extractionextracted with dichloromethane
customdried
customevaporated
customPurification by chromatography on silica gel

Sources & evidence

ORD record: ord-7273ccc9075d41eeaee7b23621d05dc7
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288096B1

Reaction notes

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