Ethanol → 4-(4-(Hexyloxy)phenyl)thiophene-2-carboxylic acid

HRID 1892087Notes

Reaction equation

[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]([CH:19]=[O:20])[S:17][CH:18]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([OH:23])C.[OH-].[Na+]>O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]([C:19]([OH:23])=[O:20])[S:17][CH:18]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of silver nitrate (4.07 g, 24 mmol), compound 1026 (1.73 g, 6 mmol), ethanol (30 mL) and aqueous sodium hydroxide solution (1M, 48 mL) was stirred at 40° C. for 3 hours and then diluted with water (150 mL). The aqueous phase was washed with ethyl acetate (2×300 mL) and acidified to pH 1 with 1N aqueous hydrochloric acid solution. The aqueous solution was extracted with EtOAc (2×300 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to yield compound 1027 (1.5 g) which was used directly in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 0.87 (m, 3H), 1.31-1.30 (m, 6H), 1.65 (m, 2H), 3.98 (m, 2H), 6.96 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.7 Hz, 2H), 8.05 (s, 2H), 13.19 (s, 1H). MS m/z=303 [M−H]−.

Workup

washThe aqueous phase was washed with ethyl acetate (2×300 mL)
extractionThe aqueous solution was extracted with EtOAc (2×300 mL)
dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-5c4ec9e80df045ea95b545d61faa545e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507647B2

Reaction notes

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