Mesityl oxide → HCID 86744883, compound

HRID 1494693Notes

Reaction equation

CC(C)([O-])C.[K+].[CH3:7][C:8]([CH3:13])=[CH:9][C:10](=[O:12])[CH3:11].S([C:18]1C=[CH:23][C:21](C)=[CH:20][CH:19]=1)([O-])(=O)=O.C(O)/C=C\CC.[NH4+].[Cl-:32]>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[Cl:32][C:9]([CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:23])([C:8]([CH3:13])=[CH2:7])[C:10](=[O:12])[CH3:11]

Participants

Conditions

Temperature: -70 °C

Procedure

2 ml of hexamethylphosphoramide was added to a solution of 1.7 g (16 millimole) of potassium t-butoxide in 15 ml of tetrahydrofuran, and cooled to -70° C. under nitrogen. 2 g (15 millimole) of the product of Step A in 4 ml tetrahydrofuran was added over the course of 5 minutes, with stirring. The stirring of the deep orange solution was continued for another 15 minutes and then a solution of 3.5 g (15 millimole) of the tosylate of cis-2-pentene-1-ol in 2 ml tetrahydrofuran was added. After 30 minutes the mixture was warmed to 0° C., maintained at that temperature for 1 hour, and then warmed to room temperature, followed by the addition of 10 ml of 1N NH4Cl. Following extraction with ether, 2.5 g of a crude, yellow-brown oil was obtained. Flash column chromatography yielded 1.1 g (16% yield) of 3-chloro-3-(cis-2-pentenyl)- 4-methyl-4-pentene-2-one: ##STR9##

Workup

stirringThe stirring of the deep orange solution
temperatureAfter 30 minutes the mixture was warmed to 0° C.
temperaturemaintained at that temperature for 1 hour
temperaturewarmed to room temperature
extractionextraction with ether, 2.5 g of a crude
customyellow-brown oil was obtained

Sources & evidence

ORD record: ord-3b67d4b00cab4c4cb53a0ae63261b7a7
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05026918

Reaction notes

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