7-(3-Hydroxyprop-1-ynyl)-3-(4-methoxyphenyl)chromen-2-one → 7-(3-Hydroxypropyl)-3-(4-methoxyphenyl)chromen-2-one

HRID 2045733Notes

Reaction equation

HRID 2045733 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1>C1COCC1>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 584024147-(3-Hydroxyprop-1-ynyl)-3-(4-methoxyphenyl)chromen-2-one

Product 1

HCID 584024107-(3-Hydroxypropyl)-3-(4-methoxyphenyl)chromen-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(3-Hydroxyprop-1-ynyl)-3-(4-methoxyphenyl)chromen-2-one is hydrogenated to completion in THF on palladium/active carbon catalyst. The catalyst is filtered off, the solvent is removed in vacuo, and the crude product is recrystallised from toluene/heptane (1:1), giving 7-(3-hydroxypropyl)-3-(4-methoxyphenyl)chromen-2-one as colourless solid.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. customthe crude product is recrystallised from toluene/heptane (1:1)

Sources & evidence

ORD record
ord-d3676b23e5e54d36bb1b60650c066ebe
Source dataset
uspto-grants-2013_11
Patent number
US08592007B2

Reaction notes

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