Potassium Carbonate → HCID 22252752, compound

HRID 1612020Notes

Reaction equation

[OH:1][C:2]1[C:3]([Se:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>O>[CH2:41]([O:40][C:38]([CH2:37][CH2:36][CH2:35][O:1][C:2]1[C:3]([Se:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=2)=[CH:4][C:5]2[C:6]([CH3:14])([CH3:15])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1)=[O:39])[CH3:42]

Participants

Conditions

Temperature: 80 °C

Procedure

432 mg (102.0 mmol) of ethyl 6-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro 2-naphthylselanyl)nicotinate, 276 mg (2 mmol) of potassium carbonate and 390 mg (2 mmol) of ethyl 4-bromobutanoate are introduced into a three-necked flask. The mixture is heated at 80° C. for 12 h. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out by settling, washed with water, dried over magnesium sulphate and evaporated. After purification by flash chromatography (9 heptane/1 EtOAc), 467 mg (85%) of the expected compound are collected in the form of an orange-coloured oil.

Workup

extractionextracted with ethyl ether
customthe organic phase is separated out
washwashed with water
dry with materialdried over magnesium sulphate
customevaporated
customAfter purification by flash chromatography (9 heptane/1 EtOAc), 467 mg (85%) of the expected compound
customare collected in the form of an orange-coloured oil

Sources & evidence

ORD record: ord-5f69751f75524db98b8d715c39e266dd
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992094B1

Reaction notes

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