Potassium Hydroxide → HCID 57682972, compound

HRID 494313Notes

Reaction equation

HRID 494313 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15](OC(C)C)=[O:16])[CH2:10]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([CH2:15][OH:16])[CH2:10]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57682961HCID 57682961, compound

Product 1

HCID 57682972HCID 57682972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

60.6 g of isopropyl (1R,3S)-3-(tetrahydropyran-2-yloxymethyl)cyclohexanecarboxylate were dissolved in 100 ml of THF and, at 0° C., were added dropwise to a suspension of 16.2 g of lithium aluminum hydride in 300 ml of THF. The mixture is stirred at RT until precursor is no longer detectable by TLC. 50 ml of 10N KOH are added to the mixture at 0° C. The solution above the gray precipitate is decanted off, and the residue is digested with ethyl acetate and filtered. The combined filtrates are evaporated, the residue is extracted with ethyl acetate, and the org. phases are dried over MgSO4 and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate gradient), resulting in 30.7 g of (1R,3S)-3-(tetrahydropyran-2-yloxymethyl)cyclo-hexylmethanol as yellow oil.

Workup

  1. customThe solution above the gray precipitate is decanted off
  2. filtrationfiltered
  3. customThe combined filtrates are evaporated
  4. extractionthe residue is extracted with ethyl acetate
  5. dry with materialphases are dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (heptane/ethyl acetate gradient)
  8. customresulting in 30.7 g of (1R,3S)-3-(tetrahydropyran-2-yloxymethyl)cyclo-hexylmethanol as yellow oil

Sources & evidence

ORD record
ord-6125eb7d201e4057a0fbb256ac3b55f3
Source dataset
uspto-grants-2009_05
Patent number
US07538131B2

Reaction notes

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