Water → HCID 565576, compound

HRID 611470Notes

Reaction equation

HRID 611470 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:19])[C:12]2([C:16](O)=[O:17])[C:13]([CH2:15][CH:9]1[CH2:10][CH2:11]2)=[O:14].O>CCOCC>[CH3:7][C:8]1([CH3:19])[CH:9]2[CH2:10][CH2:11][C:12]1([CH2:16][OH:17])[CH:13]([OH:14])[CH2:15]2

Participants

5

Reactant 3

HCID 962WaterHCID 2978887,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 565576HCID 565576, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cooled mixture of lithium aluminum hydride (4 g, 105.4 mmol) in ether was added dropwise a solution of camphorsulfonyl chloride (10 g, 39.88 mmol) and ketopinic acid, prepared as described in Step 1, above. After the addition was complete, the ice bath was removed and the mixture was stirred at ambient temperature for 2 hrs. The mixture was cooled again and wet ether was added cautiously. When the violent reaction subsided, water was added. The mixture was then extracted three times with ethyl acetate. The combined extracts were washed with water and brine and dried over anhydrous magnesium sulfate. Evaporation of the solution gave 4.8 g of a white powder. NMR(δ): 0.90 (s, 3H), 1.20 (s, 3H).

Workup

  1. customprepared
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. temperatureThe mixture was cooled again
  5. additionwet ether was added cautiously
  6. customWhen the violent reaction
  7. extractionThe mixture was then extracted three times with ethyl acetate
  8. washThe combined extracts were washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customEvaporation of the solution

Sources & evidence

ORD record
ord-c228431786e849d9b296ba6763ed91b2
Source dataset
uspto-grants-1999_12
Patent number
US06001659

Reaction notes

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