Sodium Bicarbonate → ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate

HRID 1267490Notes

Reaction equation

HRID 1267490 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]([CH2:40][CH2:41][C:42]([F:54])([F:53])[C:43]([F:52])([F:51])[C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>Cl.CO>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]([CH2:40][CH2:41][C:42]([F:54])([F:53])[C:43]([F:51])([F:52])[C:44]([F:49])([F:50])[C:45]([F:46])([F:47])[F:48])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 18546290ethyl 10-[(3RS,4RS)-7-(methoxymethoxy)-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate

Product 1

HCID 18546291ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoateYield 93.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Concentrated hydrochloric acid (10 drops) was added to a solution of ethyl 10-[(3RS,4RS)-7-(methoxymethoxy)-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate (1.33 g, 1.686 mmol) in methanol (15 ml) followed by stirring for 4 hours at 50° C. The reaction mixture was neutralized with aqueous sodium bicarbonate and then concentrated under reduced pressure. Water was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4) to give ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate (1.10 g, Yield 93%) as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue, which
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-301600ac04be4aed84df62e9d00c37c2
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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