(3-Benzyloxy-5-trifluoromethylthien-2-yl)-carboxylic acid → 3-Benzyloxy-5-trifluoromethylthiophen
Reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[S:11][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cu].N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[S:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 1F (14.5 g) and quinoline (50 ml) was treated with copper powder (4.57 g) and heated to 150° C. The reaction mixture is heated for 25 minutes at 150° C. and cooled to room temperature. The mixture was filtered and washed with water. Aqueous quinoline was acidified with 6N HCl (pH=2) and extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue was chromatographed to yield a yellow liquid (8.74 g, 71%).
Workup
- temperatureThe reaction mixture is heated for 25 minutes at 150° C.
- temperaturecooled to room temperature
- filtrationThe mixture was filtered
- washwashed with water
- extractionextracted with diethyl ether twice
- washThe combined organic phases were washed with water
- customdried
- concentrationThe mixture was concentrated
- customthe residue was chromatographed
Sources & evidence
- ORD record
- ord-63c15aaaa6004b2c8a75322f6f2acbcd
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869426
Reaction notes
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