Sodium Hydroxide → HCID 13676044, compound

HRID 392597Notes

Reaction equation

HRID 392597 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:15]1([C:18](OCC)=[O:19])[CH2:17][CH2:16]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+].[OH-].[Na+]>CCOCC>[OH:14][CH:7]([C:15]1([CH2:18][OH:19])[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 13969923HCID 13969923, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13676044HCID 13676044, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen stream, lithium aluminum hydride (4.55 g, 0.12 mol) was suspended in dehydrated ether (120 ml) and a solution (50 ml) of ethyl 1-benzoylcyclopropanecarboxylate (21.83 g, 0.1 mol) in dehydrated ether was added dropwise over 50 min while stirring under ice-cooling. The mixture was stirred at room temperature for 1.5 h, and 10% aqueous sodium hydrogen carbonate (15 ml) was slowly added dropwise under ice-cooling. Then 20% aqueous sodium hydroxide (30 ml) was added dropwise, and the mixture was stirred for 30 min. The ether layer was separated by decantation and the residue was washed twice with 30 ml of ether. The ether layer was combined, washed with saturated brine, dehydrated over anhydrous magnesium sulfate and concentrated. The residual solution (16.9 g) was purified by silica gel column chromatography (chloroform/methanol=20/1) to give the title compound (14.51 g) as a colorless oil (yield 81%).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1.5 h
  3. temperaturecooling
  4. stirringthe mixture was stirred for 30 min
  5. customThe ether layer was separated by decantation
  6. washthe residue was washed twice with 30 ml of ether
  7. washwashed with saturated brine
  8. concentrationconcentrated
  9. customThe residual solution (16.9 g) was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-61e7636eb06040af80eb45b727c01ea8
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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