Tetrahydrofuran → HCID 21459436, compound

HRID 1941027Notes

Reaction equation

HRID 1941027 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]2[CH2:22][O:21][C:20]3([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[O:19]2)[CH2:14][CH2:13]1)=O)C.C1C[O:31][CH2:30]C1>>[O:19]1[C:20]2([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[O:21][CH2:22][CH:18]1[CH:15]1[CH2:14][CH2:13][CH:12]([CH2:10][CH2:30][OH:31])[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 67582984HCID 67582984, compound

Product 1

HCID 21459436HCID 21459436, compound

Conditions

Temperature
0 °C

Procedure

Dried THF (100 ml) was added to lithium aluminum hydride (17.6 g, 0.464 mol), followed by cooling the mixture down to 0° C., dropwise adding thereto a 800 ml THF solution of the above 4-(1,4-dioxaspiro[4.5]decyl)cyclohexylmethanoic acid ethyl ester (183.2 g, 0.464 mol), stirring at 0° C. for 3 hours, stirring at room temperature for 2 hours, washing the reaction solution successively with 3N HCl, a saturated aqueous solution of sodium bicarbonate and water, distilling off the solvent, and recrystallizing, to isolate colorless crystals of 2-(4-(1,4-dioxaspiro[4,5]decyl)cyclohexyl)ethanol (50.6 g, 0,179mol). Yield from bicyclohexanedione monoethylene ketal was 38%.

Workup

  1. additiondropwise adding
  2. washwashing the reaction solution successively with 3N HCl
  3. distillationa saturated aqueous solution of sodium bicarbonate and water, distilling off the solvent
  4. customrecrystallizing

Sources & evidence

ORD record
ord-3d05d85e11a34016bf3540b086cbf284
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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