N-methyl-2-pyrrolidone → HCID 18324245, compound

HRID 1251609Notes

Reaction equation

CN1CCCC1=O.Br[C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2=[O:18])=[CH:11][CH:10]=1.C([Sn](CCCC)(CCCC)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)CCC.[F-].[K+]>O.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[Pd]Cl>[C:24]1([C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][CH2:14][C:15]3=[O:18])=[CH:11][CH:10]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a three-necked flask of 500 ml, fitted with a condenser, was added 150 ml N-methylpyrrolidon (NMP), 10.45 g (49.5 mmol) 6-bromoindan-1-one and 19.9 g (54.2 mmol) of tributylphenyltin. To this mixture was added 1.05 g (1.50 mmol) of bis(triphenyl-phosphine)palladium(II)chloride. The reaction mixture was heated to 85° C. for 4 h, followed by stirring for 4 hours at ambient temperature. A solution of 23 g of potassiumfluoride in 50 ml of water was added. The solids were filtered off and the filtrate was diluted with diethylether, washed once with water and once with saturated sodiumchloride solution. The ether layer was evaporated under reduced pressure and the solid material was crystallised from toluene, petroleum ether. A total of 5.29 g of 6-phenylindan-1-one was obtained, yield 51.4%.

Workup

customTo a three-necked flask of 500 ml, fitted with a condenser
filtrationThe solids were filtered off
additionthe filtrate was diluted with diethylether
washwashed once with water and once with saturated sodiumchloride solution
customThe ether layer was evaporated under reduced pressure
customthe solid material was crystallised from toluene, petroleum ether

Sources & evidence

ORD record: ord-0ff71c9242484a28aeb17bb789fb3937
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06342622B1

Reaction notes

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