(Diethylamino)sulfur trifluoride → 2-(p-Octyloxyphenyl)-5-(3-fluoro-6-oxanonyl)pyridine

HRID 275248Notes

Reaction equation

HRID 275248 reaction equation
CCN(S(F)(F)[F:7])CC.[CH2:10]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33](O)[CH2:34][CH2:35][O:36][CH2:37][CH2:38][CH3:39])=[CH:27][N:26]=2)=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(OC1C=CC(C2C=CC(C)=CN=2)=CC=1)CCCCCCC.[Li+].CC([N-]C(C)C)C.O1C(CCOCCC)C1>C(Cl)Cl>[CH2:10]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33]([F:7])[CH2:34][CH2:35][O:36][CH2:37][CH2:38][CH3:39])=[CH:27][N:26]=2)=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 5

HCID 123472(Diethylamino)sulfur trifluorideHCID 2724682Lithium diisopropylamideHCID 14766021HCID 14766021, compoundHCID 20087453HCID 20087453, compoundHCID 20087472HCID 20087472, compound

Product 1

HCID 200874582-(p-Octyloxyphenyl)-5-(3-fluoro-6-oxanonyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.11 mol of DAST is added at -30° C. to a solution of 0.1 mol of 2-(p-octyloxyphenyl)-5-(3-hydroxy-6-oxanonyl)pyridine (obtainable by reaction of 2-(p-octyloxyphenyl)-5-methylpyridine with LDA at -40° C. and optically active 1,2-epoxy-5-oxaoctane) in methylene chloride, and the reaction mixture is then warmed slowly to room temperature. After 12 hours, the mixture is subjected to customary work-up, and the product is purified by crystallization, to give optically active 2-(p-octyloxyphenyl)-5-(3-fluoro-6-oxanonyl)pyridine.

Workup

  1. customthe product is purified by crystallization

Sources & evidence

ORD record
ord-0ad77c38dd8d46db814e649beac6acc5
Source dataset
uspto-grants-1995_02
Patent number
US05393459

Reaction notes

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