4-(3-Methoxy-prop-1-ynyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester → 4-(3-Methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29468Notes

Reaction equation

HRID 29468 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[C:17][CH2:18][O:19][CH3:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]>[Pd].O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][CH2:18][O:19][CH3:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 687129474-(3-Methoxy-prop-1-ynyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687130034-(3-Methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(3-methoxy-prop-1-ynyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (2.6566 g, 0.00977 mol, Example 22, Step 1) and 10% palladium on activated carbon (705 mg) and tetrahydrofuran (60 mL) was stirred under a hydrogen atmosphere (balloon) for 20 hours. After filtering the mixture through a celite pad the resulting solution was reduced to dryness furnishing 2.46 g (91%) of of 4-(3-methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester as a clear oil. MS (ES) m/z: 277.1 (M+H)+, 553.3 (2M+H).

Workup

  1. filtrationAfter filtering the mixture through a celite pad the resulting solution

Sources & evidence

ORD record
ord-05cbdda67cd94ea8aca8e64fec32e5ca
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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