HCID 13593934, compound → 1-(2-Hydroxyethyl)cyclopentan-1-ol

HRID 2200587Notes

Reaction equation

HRID 2200587 reaction equation
[OH:1][C:2]1([CH2:7][C:8](OC(C)(C)C)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:9][CH2:8][CH2:7][C:2]1([OH:1])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 13593934HCID 13593934, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 141019991-(2-Hydroxyethyl)cyclopentan-1-olYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(1-hydroxycyclopentyl)acetate (0.5 g, 2.5 mmol) in THF (10 mL) was added lithium aluminium hydride (0.28 g, 7.5 mmol) portionwise at 0° C. The reaction was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (1:1) to give 1-(2-hydroxyethyl)cyclopentanol (0.33 g, 100%) as a yellow oil.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product which
  6. customwas purified by column chromatography
  7. washeluting with petroleum ether/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-bb88191fbb334af3a0dfca3ee89ada6f
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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