Isopropanol → HCID 18649406, compound

HRID 1653989Notes

Reaction equation

HRID 1653989 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH2:9][CH:10]2[C:17](=O)[O:16][C:14](=[O:15])[CH:11]2[CH2:12][CH:13]=1.C(OCC)(=O)C.C(O)(C)C>O1CCCC1.O>[CH3:7][C:8]1[CH2:9][C@H:10]([CH2:17][OH:16])[C@H:11]([CH2:14][OH:15])[CH2:12][CH:13]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 984963a,4,7,7a-Tetrahydro-5-methyl-1,3-isobenzofurandioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18649406HCID 18649406, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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-1,2dicarboxylic 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 isopropanol 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. NMR (CDCl3): 5.35 (br s,1H), 3.68 (m,2H), 3.60 (m,2H), 3.10 (br s,2H), 2.05 (br s,6H), 1.64 (s,3H). IR (neat): 3500-3100, 1730w, 1440, 1010. MS (CI): 157 (M+I), 139,121.

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-539dcdb16add40e091528bb6b8e50f10
Source dataset
uspto-grants-1995_04
Patent number
US05405830

Reaction notes

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