Sodium Hydroxide → HCID 21101214, compound

HRID 1352851Notes

Reaction equation

HRID 1352851 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](OCC)=[O:12])=[CH:5][C:4]=1[O:16][CH2:17][O:18][CH3:19].[OH-].[Na+]>C1(C)C=CC=CC=1.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11][OH:12])=[CH:5][C:4]=1[O:16][CH2:17][O:18][CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89258928HCID 89258928, compound

Product 1

HCID 21101214HCID 21101214, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of the compound (4.54 g, 17.0 mmol) of Example 9-2 in toluene (60 ml) was stirred at −78° C., and thereto was dropped diisobutylalminumhydride (1.0M in hexane: 35.8 ml, 35.8 mmol). The mixture was stirred for 1.5 hours at −78° C., followed by addition of an aqueous 2N sodium hydroxide solution. The precipitate was filtered off and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and an aqueous sodium chloride solution in the order, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the subject compound (3.65 g, 95.7%).

Workup

  1. filtrationThe precipitate was filtered off
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous sodium chloride solution in the order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-02cfd4d2298b4381a26ca2fb55c4e089
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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