HCID 22033011, compound → HCID 22033338, compound

HRID 1792411Notes

Reaction equation

HRID 1792411 reaction equation
[F:1][C:2]([F:51])([C:47]([F:50])([F:49])[F:48])[CH2:3][CH2:4][C:5]([CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[C:31]2[C:26](=[CH:27][C:28]([O:32]COC)=[CH:29][CH:30]=2)[O:25][CH2:24][C:23]1([C:37]1[CH:42]=[CH:41][C:40]([O:43]COC)=[CH:39][CH:38]=1)[CH3:36])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6]>C(O)C.Cl.C(OCC)(=O)C>[F:51][C:2]([F:1])([C:47]([F:48])([F:49])[F:50])[CH2:3][CH2:4][C:5]([CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[C:31]2[C:26](=[CH:27][C:28]([OH:32])=[CH:29][CH:30]=2)[O:25][CH2:24][C:23]1([C:37]1[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=1)[CH3:36])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6]

Participants

5

Reactant 1

HCID 22033011HCID 22033011, compound

Product 1

HCID 22033338HCID 22033338, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-11-[(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]undecanoate (128 mg, 0.17 mmol) in ethyl alcohol (5 ml), was added concentrated aqueous hydrochloric acid (10 drops) at room temperature under N2 atmosphere. The mixture was stirred at room temperature continued for 2.5 days and diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated in vacuum. Crude product was purified by flash chromatography on silica gel (hexane:ethyl acetate=3:2) to give ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-11-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl]undecanoate as a colorless glassy oil. yield: 102 mg (94%).

Workup

  1. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuum
  4. customCrude product was purified by flash chromatography on silica gel (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-bba4881519bd4898a0f1cb168e48df4a
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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