2-Bromo-5-hydroxypyridine → trans-4-[(6-Bromopyridin-3-yl)oxy]tetrahydrofuran-3-ol

HRID 2060809Notes

Reaction equation

HRID 2060809 reaction equation
[Br:1][C:2]1C=[CH:13][C:5]([O:6][C@@H:7]2[CH2:11][O:10][CH2:9][C@H:8]2[OH:12])=[CH:4][CH:3]=1.BrC1[N:21]=CC(O)=CC=1>>[Br:1][C:2]1[N:21]=[CH:13][C:5]([O:6][C@@H:7]2[CH2:11][O:10][CH2:9][C@H:8]2[OH:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27628652-Bromo-5-hydroxypyridineHCID 67195067trans-4-(4-Bromophenoxy)tetrahydrofuran-3-ol

Product 1

HCID 86653035trans-4-[(6-Bromopyridin-3-yl)oxy]tetrahydrofuran-3-ol

Procedure

The title compound of Step 1 was prepared according to the general procedure for the synthesis of trans-4-(4-bromophenoxy)tetrahydrofuran-3-ol in Example 2, except that 6-bromopyridin-3-ol was used in place of 4-bromophenol, and the crude product was purified by silica gel chromatography (Gradient: 20% to 70% ethyl acetate in heptane). Yield: 5.24 g, 20.2 mmol, 61%. 1H NMR (500 MHz, CDCl3) δ 3.79 (dd, J=9.9, 1.9 Hz, 1H), 3.87 (dd, J=10.4, 1.8 Hz, 1H), 4.00 (dd, J=9.9, 4.3 Hz, 1H), 4.19 (dd, J=10.4, 4.7 Hz, 1H), 4.38 (br m, 1H), 4.59 (br s, 1H), 4.68 (br d, J=4.4 Hz, 1H), 7.14 (dd, J=8.7, 3.2 Hz, 1H), 7.32 (dd, J=8.7, 0.5 Hz, 1H), 8.01 (br d, J=3.1 Hz, 1H).

Workup

  1. customthe crude product was purified by silica gel chromatography (Gradient: 20% to 70% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-3a5375cda64f49f690ac9bd5e307efed
Source dataset
uspto-grants-2012_10
Patent number
US08278457B2

Reaction notes

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