1,4-Dimethoxy-2-butyne → 2-(Trifluoroacetylamino)-5,6-bis(methoxymethyl)indane

HRID 244764

Reaction equation

[CH3:1][O:2][CH2:3][C:4]#[C:5][CH2:6][O:7][CH3:8].[F:9][C:10]([F:22])([F:21])[C:11]([NH:13][CH:14]([CH2:18][C:19]#[CH:20])[CH2:15][C:16]#[CH:17])=[O:12]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C(O)C>[F:9][C:10]([F:21])([F:22])[C:11]([NH:13][CH:14]1[CH2:15][C:16]2[C:19](=[CH:20][C:5]([CH2:6][O:7][CH3:8])=[C:4]([CH2:3][O:2][CH3:1])[CH:17]=2)[CH2:18]1)=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

According to the procedure of Magnus et. al (Tetrahed. Lett., 34, 23-26 (1993)) a solution of commercially available 1,4-dimethoxy-2-butyne (1.32 g, 11.5 mmol) in nitrogen-degassed ethanol is heated to 80° C. with stirring under a nitrogen atmosphere. Tris(triphenylphosphine)rhodium chloride (64 mg, 0.07 mmol) and a solution of 2,2,2-trifluoro-N-[1-(2-propynyl)-3-butynyl]acetamide (470 mg, 2.32 mmol; prepared from literature procedure: Romero, Arthur G.; Leiby, Jeffrey A PCT Int. Appl. WO 9623760) in nitrogen-degassed ethanol (2 ml) are added in portions over 2 hours. The mixture is stirred under nitrogen at 80° C. for a further 3 hours. The solvent is removed under vacuo and the residue is purified by flash chromatography on silica gel, eluting with hexane/ethyl acetate (2:1)

Workup

customdegassed ethanol
additionare added in portions over 2 hours
stirringThe mixture is stirred under nitrogen at 80° C. for a further 3 hours
customThe solvent is removed under vacuo
customthe residue is purified by flash chromatography on silica gel
washeluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record: ord-d1e3738b3d614f448ccc1ba0f93fc96c
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658673B2

Linked notes

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