2-Bromomethylnaphthalene → 4-Methoxy-4-[3-((1,2-dihydro-1-methyl-2-oxoquinolin-6-yl)methoxy)-trans-prop-1-enyl]tetrahydropyran

HRID 326232Notes

Reaction equation

HRID 326232 reaction equation
[CH3:1][O:2][C:3]1([C:9]#[C:10][CH2:11][OH:12])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH3:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH2:24]Br)=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]1=[O:26].BrCC1C=CC2C(=CC=CC=2)C=1>>[CH3:1][O:2][C:3]1(/[CH:9]=[CH:10]/[CH2:11][O:12][CH2:24][C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:14]([CH3:13])[C:15](=[O:26])[CH:16]=[CH:17]3)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 703202-BromomethylnaphthaleneHCID 151990656-(Bromomethyl)-1-methylquinolin-2(1H)-oneHCID 193880394-Methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran

Product 1

HCID 151990664-Methoxy-4-[3-((1,2-dihydro-1-methyl-2-oxoquinolin-6-yl)methoxy)-trans-prop-1-enyl]tetrahydropyran

Procedure

The desired compound was prepared according to the method of Example 1, step 4, except substituting 4-methoxy-4-(3-hydroxy-trans-prop-1-enyl)tetrahydropyran, prepared as in Example 3, for 4-methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran, and substituting 1,2-dihydro-1-methyl-2-oxo-6-(bromomethyl)quinoline for 2-(bromomethyl)naphthalene. 1H NMR (300 MHz, CDCl3); 7.67 (1H, d, J=9 Hz), 7.52-7.58 (2H, m), 7.35 (1H, d, J=9 Hz), 6.72 (1H, d, J=9 Hz), 5.75 (1H, dt, J=15.5,8 Hz), 5.63 (1H, br d, J=16 Hz), 4.60 (2H, s), 4.10 (2H, dd, J=8,1 Hz), 3.67-3.8 (4H, m), 3.15 (3H, s), 1.72-1.77 (4H, m); MS (M+H)+ =344. Analysis calc'd for C20H25NO4 : C, 69.95; H, 7.34; N, 4.08; Found: C, 69.68; H, 7.16; N, 3.99

Workup

  1. custom4-methoxy-4-(3-hydroxy-trans-prop-1-enyl)tetrahydropyran, prepared as in Example 3

Sources & evidence

ORD record
ord-cdef066247c9446d8df229457b3f3a60
Source dataset
uspto-grants-1993_12
Patent number
US05268379

Reaction notes

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