HCID 86592498, compound → HCID 86592497, compound

HRID 1792413Notes

Reaction equation

HRID 1792413 reaction equation
[F:1][C:2]([F:48])([C:44]([F:47])([F:46])[F:45])[CH2:3][CH2:4]/[CH:5]=[C:6](\[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[C:28]2[C:23](=[CH:24][C:25]([O:29]COC)=[CH:26][CH:27]=2)[O:22][CH2:21][C:20]1([C:34]1[CH:39]=[CH:38][C:37]([O:40]COC)=[CH:36][CH:35]=1)[CH3:33])/[C:7]([OH:9])=[O:8]>C(O)C.Cl.O>[F:48][C:2]([F:1])([C:44]([F:45])([F:46])[F:47])[CH2:3][CH2:4]/[CH:5]=[C:6](\[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[C:28]2[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=2)[O:22][CH2:21][C:20]1([C:34]1[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=1)[CH3:33])/[C:7]([OH:9])=[O:8]

Participants

5

Reactant 1

HCID 86592498HCID 86592498, compound

Product 1

HCID 86592497HCID 86592497, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of (E)-6,6,7,7,7-pentafluoro-2-{9-[(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]nonyl}-2-heptenoic acid (111 mg, 0.16 mmol) in ethyl alcohol (5 ml), was added 6 N aqueous solution of hydrochloric acid (30 drops) and the reaction mixture was stirred at 40° C. for 6 h. The reaction mixture was diluted with water and extracted with methylene chloride. Organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuum. Crude product was purified by flash chromatography on silica gel (hexane:ethyl acetate:methyl alcohol=10:10:1), and then additionally by preparative thin-layer chromatography on Merck Silica-gel 60 plates (hexane:ethyl acetate:methyl alcohol=5:5:1) to give (E)-6,6,7,7,7-pentafluoro-2-{9-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methychroman-4-yl]nonyl}-2-heptenoic acid as a colorless amorphous solid. yield: 47.4 mg (49%)

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialOrganic extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuum
  4. customCrude product was purified by flash chromatography on silica gel (hexane:ethyl acetate:methyl alcohol=10:10:1)

Sources & evidence

ORD record
ord-64820e20b2e1429798acad9ad3103b90
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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