Tetrahydrofuran → HCID 12094540, compound

HRID 2120156Notes

Reaction equation

HRID 2120156 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([C:23]1[C:24](C)=[C:25](C)[C:26]2[C:30]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)=[C:29](O[SiH3])[O:28][C:27]=2[CH:39]=1)(C)(C)C.C1C[O:45]CC1>>[N:33]1[CH:34]=[CH:35][CH:36]=[C:31]([C:30]2[C:26]3[CH:25]=[CH:24][C:23]([OH:45])=[CH:39][C:27]=3[O:28][CH:29]=2)[CH:32]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 137329725HCID 137329725, compound

Product 1

HCID 12094540HCID 12094540, compoundYield 79%

Procedure

1M tetrabutylammonium fluoride solution in THF (16 ml, 16.00 mmol) was added to a THF (150 ml) solution of 3-(6-t-butyldimethyl silyloxybenzo[b]furan-3-yl)pyridine (5.2 g, 15.88 mmol) obtained above, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was concentrated under reduced pressure and the resulting concentrate was charged to short path silica gel column chromatography (chloroform:ethyl acetate=1:1-1:2). A white powder of 3-(3- pyridyl)benzo[b]furan-6-ol (2.7g, 79%) was then obtained by crystallization using ether-hexane.

Workup

  1. customobtained above, and the mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. concentrationthe resulting concentrate
  4. additionwas charged to short path silica gel column chromatography (chloroform:ethyl acetate=1:1-1:2)

Sources & evidence

ORD record
ord-899fd497a88840539ecadd028af97883
Source dataset
uspto-grants-2004_02
Patent number
US06689798B2

Reaction notes

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