Ammonium Hydroxide → 2-{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetamide

HRID 751490Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:10][C:11]1[C:16]2[CH:17]=[CH:18][O:19][C:15]=2[C:14]([CH2:20][C:21]([OH:23])=O)=[CH:13][CH:12]=1.[OH-].[NH4+:25]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:10][C:11]1[C:16]2[CH:17]=[CH:18][O:19][C:15]=2[C:14]([CH2:20][C:21]([NH2:25])=[O:23])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Combine {4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid (0.920 g, 2.872 mmol), and 1,1-carbonyldiimidazole (2.365 g, 14.585 mmol) in tetrahydrofuran (15 ml), and stir for 1 hour under nitrogen. Cool the mixture to 0° C., and add concentrated aqueous ammonium hydroxide (2 ml). Remove the ice bath, and stir the mixture at room temperature for 16 hours. Dilute the mixture with ethyl acetate, wash with water and brine, dry over sodium sulfate, filter, and concentrate. Purification using flash chromatography and eluting with hexane:ethyl acetate gives 0.732 g (80%) of the title product as a white solid. Mass spectrum: electrospray (m/z) 236 (M++1-85).

Workup

customRemove the ice bath
additionDilute the mixture with ethyl acetate
washwash with water and brine
dry with materialdry over sodium sulfate
filtrationfilter
concentrationconcentrate
customPurification
washeluting with hexane

Sources & evidence

ORD record: ord-16215c1e28164e1996bddbb55146c962
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405305B2

Reaction notes

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