Tetrahydrofuran → HCID 86749701, compound

HRID 1077411Notes

Reaction equation

O1C[CH2:4][CH2:3][CH2:2]1.[C:6]1([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrCCC[N:44]1[C:48](=[O:49])[C:47]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:46]2[C:45]1=[O:54]>C(OCC)(=O)C>[C:12]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:19]=[CH:18][C:15]([CH:16]=[CH:2][CH2:3][CH2:4][C:52]2[CH:53]=[C:46]3[C:45](=[O:54])[NH:44][C:48](=[O:49])[C:47]3=[CH:50][CH:51]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A suspension of 150 ml of tetrahydrofuran, 5.46 g of 4-phenylbenzaldehyde and 15.9 g of N-(3-bromopropyl)-phthalimide triphenyl phosphonium bromide was cooled to -40° C. and 3.37 g of potassium terbutylate was then introduced. The temperature was allowed to rise to -15° C. and the mixture was stirred at -15° C. for one hour. The mixture was poured over ice and extraction was carried out with ethyl acetate. The extracts were washed with water and the organic phases were dried over Na2SO4, filtered and concentrated to obtain 19 g of product which was dissolved in methylene chloride. Chromatography on silica was carried out, eluting with an ethyl acetate - hexane mixture (3-7) and the residue was concentrated, impasted in hexane, followed by separation and drying under reduced pressure to obtain 8.5 g of the desired product melting at approximately 112°-114° C.

Workup

customto rise to -15° C.
additionThe mixture was poured over ice and extraction
washThe extracts were washed with water
dry with materialthe organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f360c0c79cc24f4a987fa42d354e8de6
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05543400

Reaction notes

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