Hydrochloric Acid → HCID 86592498, compound

HRID 1792412Notes

Reaction equation

HRID 1792412 reaction equation
[F:1][C:2]([F:50])([C:46]([F:49])([F:48])[F:47])[CH2:3][CH2:4]/[CH:5]=[C:6](\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([O:31][CH2:32][O:33][CH3:34])=[CH:28][CH:29]=2)[O:24][CH2:23][C:22]1([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=1)[CH3:35])/[C:7]([O:9]CC)=[O:8].Cl>C(O)C.[OH-].[K+]>[F:50][C:2]([F:1])([C:46]([F:47])([F:48])[F:49])[CH2:3][CH2:4]/[CH:5]=[C:6](\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([O:31][CH2:32][O:33][CH3:34])=[CH:28][CH:29]=2)[O:24][CH2:23][C:22]1([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:40][CH:41]=1)[CH3:35])/[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86592499HCID 86592499, compound

Product 1

HCID 86592498HCID 86592498, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of ethyl (E)-6,6,7,7,7-pentafluoro-2-{9-[(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]nonyl}-2-h eptenoate (116 mg, 0.16 mmol) in ethyl alcohol (5 ml), 5 N aqueous potassium hydroxide solution was added and the mixture was stirred under N2 atmosphere at 70° C. for 5 h. After cooling to room temperature the reaction mixture was acidified by 6 N aqueous hydrochloric acid and extracted with methylene chloride. Extracts were dried over anhydrous sodium sulfate and concentrated in vacuum to give crude (E)-6,6,7,7,7-pentafluoro-2-{9-[(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]nonyl}-2-heptenoic acid as a colorless oil. yield: 111 mg (quant.). The sample was used in the following step without further purification.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. extractionextracted with methylene chloride
  3. dry with materialExtracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-5622d29f00734a1982d17b4dcd5b87fc
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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