Tetrahydropyran → HCID 57151154, compound

HRID 1654500Notes

Reaction equation

[O:1]1[CH2:6][CH2:5]C[CH2:3][CH2:2]1.[CH3:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][O:19][C:20]3[CH:21]=[C:22]([CH2:26][C:27]#[N:28])[CH:23]=[CH:24][CH:25]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:29]>>[C:27]([C:26]1([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:18][C:14]3[CH:13]=[C:12]4[C:17](=[CH:16][CH:15]=3)[N:8]([CH3:7])[C:9](=[O:29])[CH:10]=[CH:11]4)[CH:21]=2)[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)#[N:28]

Participants

Reactant 2

HCID 8894Tetrahydropyran

HCID 57153655HCID 57153655, compound

Product 1

HCID 57151154HCID 57151154, compoundYield 61%

Procedure

Using the procedure described in the third paragraph of the portion of Example 2 which is concerned with the preparation of 4-ethoxycarbonyl-4-(3-hydroxypheny])tetrahydropyran, 3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-ylmethoxy)phenylacetonitrile was reacted with bis-2-chloroethyl ether to give 4-cyano-4-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-ylmethoxy)phenyl]tetrahydropyran in 61% yield, m.p. 149°-150° C. (recrystallised from a mixture of methylene chloride and diethyl ether).

Sources & evidence

ORD record: ord-6c59f927710046658ea272315f72134f
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05407945

Reaction notes

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