Iodoethane → HCID 20063997, compound

HRID 359859Notes

Reaction equation

[CH:1]([N-]C(C)C)(C)[CH3:2].[Li+].[Cl:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([Cl:20])[C:18]=1[CH3:19])[C:13]([OH:15])=[O:14].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[O:31][N:30]=[C:29]([CH3:32])[CH:28]=1.C(I)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.CN(C)P(N(C)C)(N(C)C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([Cl:20])[C:18]=1[CH2:19][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[O:31][N:30]=[C:29]([CH3:32])[CH:28]=1)[C:13]([O:15][CH2:1][CH3:2])=[O:14]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1.2 ml hexamethylphosphoramide and 6.7 ml 1.75M lithium diisopropylamide in 9 ml tetrahydrofuran at 0° C. under nitrogen was slowly added a solution of 1.00 g 3,5-dichloro-4-methylbenzoic acid in 3 ml tetrahydrofuran. After 1 hr the solution was cooled to -78° C. and 1.00 g 5-(5-bromopentyl)-3-methylisoxazole was added. The reaction mixture was stirred at room temperature for 19 hrs and worked up by acid-base extraction to give 1.3 g crude acid product. The latter was treated with 1 ml ethyl iodide and 4.9 g potassium carbonate in 10 ml dimethylformamide, stirred 12 hrs at room temperature. Extraction with ether and washing with water provided 1 g of ethyl 3,5-dichloro-4-[6-(3-methyl-5-isoxazolyl)hexyl]benzoate suitable for subsequent reactions.

Workup

extractionworked up by acid-base extraction
customto give 1.3 g crude acid product
stirringstirred 12 hrs at room temperature
extractionExtraction with ether
washwashing with water

Sources & evidence

ORD record: ord-3c081daa015c43acaf04c9a1c97bbaca
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05002960

Reaction notes

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