Water → HCID 18649406, compound

HRID 1682174Notes

Reaction equation

HRID 1682174 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C:8]1[CH:9]2[C:17](=[O:18])[O:16][C:14](=O)[CH:10]2[CH2:11][CH2:12][CH:13]=1.[C:19](OCC)(=O)C.O>O1CCCC1>[CH3:19][C:12]1[CH2:11][C@H:10]([CH2:14][OH:16])[C@H:9]([CH2:17][OH:18])[CH2:8][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 54253834HCID 54253834, compound

Product 1

HCID 18649406HCID 18649406, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 300 ml of tetrahydrofuran at 0° C. was added 16.0 g (0.42 mol) lithium aluminum hydride portionwise keeping the reaction temperature between 0° C. and 5° C. A solution of 33.0 g (0.20 mol) of 4-methyl-4-cyclohexene-2,3-dicarboxylic anhydride in 100 ml of tetrahydrofuran was added dropwise over 2 hours keeping the temperature between 0° C. and 10° C. The reaction mixture was warmed to ambient temperature and stirred for 2 hours. The reaction was cooled to 0° C. and 35 ml of ethyl acetate was added dropwise, followed by dropwise addition of 35 ml isoropanol and 35 ml water. The reaction mixture was filtered through celite using acetone, dried with MgSO4, filtered, and concentrated to 33.0 g of oil. Flash chromatography in 3:1 hexanes-ethylacetate, followed by 1:1 hexanes-ethylacetate and finally ethylacetate alone yielded 18.2 g of oil.

Workup

  1. customthe reaction temperature between 0° C. and 5° C
  2. customthe temperature between 0° C. and 10° C
  3. temperatureThe reaction was cooled to 0° C.
  4. filtrationThe reaction mixture was filtered through celite
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to 33.0 g of oil

Sources & evidence

ORD record
ord-722fa9ba00904a90b697e5d6f0698a2d
Source dataset
uspto-grants-1992_12
Patent number
US05175314

Reaction notes

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