Hydrochloric Acid → HCID 67485090, compound

HRID 660987Notes

Reaction equation

HRID 660987 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH2:34][CH:35]=[CH2:36])([CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[C:18]([CH3:33])[CH:17]=2)[CH2:11][CH:12]=[CH2:13])=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1>[CH2:11]([C:10]([C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)([CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH3:33])[C:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=2)=[C:20]([CH3:22])[CH:21]=1)[CH2:34][CH:35]=[CH2:36])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59356046HCID 59356046, compound

Product 1

HCID 67485090HCID 67485090, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-thiophene-2-carboxylic acid methyl ester (0.186 g, 0.361 mmol) in THF (4.0 mL) is treated with LiOH (1N aqueous, 4.0 mL, 4.0 mmol), warmed to 70° C., and stirred overnight. The reaction mixture is cooled to rt., acidified with HCl (1N aqueous, 4.2 mL), and extracted with EtOAc (3×10 mL). The combined extracts are dried over MgSO4, filtered, and conc. to provide 5-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-thiophene-2-carboxylic acid (0.171 g, 94%) as a white foam. MS (ES): 501.4 [M+H]+.

Workup

  1. temperatureThe reaction mixture is cooled to rt
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined extracts are dried over MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9b17b99496d048d5aec4d9dd5c15b356
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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