tert-Butyl (triphenylphosphoranylidene) acetate → HCID 44139028, compound

HRID 883806Notes

Reaction equation

[CH3:1]/[C:2](=[CH:5]\[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)/[CH:3]=O.[C:15]([O:19][C:20]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>C(#N)C>[CH3:1]/[C:2](=[CH:5]\[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)/[CH:3]=[CH:22]/[C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21]

Participants

Conditions

Temperature: 65 °C

Procedure

(E)-2-Methyl-3-(4-nitrophenyl)prop-2-enal (3.0 g, 15.6 mmol), (tert-butoxycarbonyl methylene)triphenylphosphorane (8.85 g, 23.4 mmol) and dry acetonitrile (60 ml) were stirred and heated at 65° C. until reaction was complete (ca. 1 h, HPLC monitoring). The mixture was cooled, filtered to remove some insoluble by-product, and the filtrate concentrated in vacuo to ca. 15 ml volume. On cooling the product deposited, was collected by filtration and washed with cold acetonitrile to give a yellow solid (2.4 g), mp 120-122° C. The mother liquors were evaporated to dryness, the residue stirred in ether (20 ml) and the insoluble material removed by filtration. The filtrate was concentrated in vacuo and the residue crystallised from acetonitrile (5 ml) to give a second crop of product (1.3 g). Total yield=3.7 g (87%)

Workup

custom(ca. 1 h, HPLC monitoring)
temperatureThe mixture was cooled
filtrationfiltered
customto remove some insoluble by-product
concentrationthe filtrate concentrated in vacuo to ca. 15 ml volume
temperatureOn cooling the product
filtrationwas collected by filtration
washwashed with cold acetonitrile

Sources & evidence

ORD record: ord-1e747d2fc4224f7595787040f03c439b
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236985B2

Reaction notes

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