Sodium Hydroxide → HCID 21082765, compound

HRID 347330Notes

Reaction equation

HRID 347330 reaction equation
C([O:9][C@H:10]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[C:25]1([C@@H:10]([OH:9])[C@H:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58708321HCID 58708321, compound

Product 1

HCID 21082765HCID 21082765, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 7S (2.11 g, 5.24 mmol) was added a solution of sodium hydroxide (295 mg, 7.38 mmol) in methanol (10.5 ml). After stirring for 18 h at rt, the reaction mixture was concentrated in vacuo. After addition of water, the product was extracted with dichloromethane twice and the organic layer was dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was purified by silica gel chromatography (eluted with 8:1 hexane:AcOEt) to give 8S (1.25 g, 80%) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionAfter addition of water
  3. extractionthe product was extracted with dichloromethane twice
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter concentration in vacuo
  6. customthe residue was purified by silica gel chromatography (eluted with 8:1 hexane:AcOEt)

Sources & evidence

ORD record
ord-ed673eb2750b4c7aa46efba49969b5ac
Source dataset
uspto-grants-2007_02
Patent number
US07173141B2

Reaction notes

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