Sodium Hydroxide → 1318951-91-5

HRID 2068666Notes

Reaction equation

HRID 2068666 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:12]1([C:18](OC)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].[OH-].[Na+].[NH4+].[Cl-]>CCOCC.O>[CH2:7]([C:12]1([CH2:18][OH:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 67328569HCID 67328569, compound

Product 1

HCID 573169791318951-91-5Yield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

LiAlH4 (15 mL, 30 mmol, 2 M/THF) was added drop wise to a solution of 2-2 (1.773 g, 12.5 mmol) in ether (9 mL) at a rate to maintain a gentle reflux. The mixture was stirred further for 15 min. and then was cooled to 0° C. H2O (1 mL) was added followed by 3 M NaOH (1.2 mL) and more H2O (3 mL). The resulting mixture was allowed to warm to room temperature and after 1 h of stirring, 50 mL saturated NH4Cl solution was added. The mixture was extracted with dichloromethane (3×30 mL) and the combined dichloromethane solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography using a combiflash system by Teledyne Isco (80 g silica gel, 0→100% ethyl acetate/hexanes) which gave the title compound (968 mg, 5.3 mmol, 42%).

Workup

  1. temperatureto maintain a gentle reflux
  2. temperatureto warm to room temperature and after 1 h
  3. stirringof stirring
  4. extractionThe mixture was extracted with dichloromethane (3×30 mL)
  5. washthe combined dichloromethane solution was washed with brine
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-45ee1c71f0f9409992d1a9d33d2b1020
Source dataset
uspto-grants-2012_10
Patent number
US08299068B2

Reaction notes

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