HCID 21057711, compound → HCID 21941394, compound

HRID 1158900Notes

Reaction equation

HRID 1158900 reaction equation
C[O:2][C:3]([C:5]1[O:9][C:8]2[CH2:10][CH2:11][CH2:12][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:9]1[C:5]([CH2:3][OH:2])=[CH:6][C:7]2[CH2:12][CH2:11][CH2:10][C:8]1=2

Participants

4

Reactant 2

HCID 21057711HCID 21057711, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21941394HCID 21941394, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5,6-Dihydro-4H-cyclopenta[b]furan-2-carboxylic acid methyl ester (2.24 g) was added to the THF (59 mL) solution of LiAlH4 (511 mg) under a nitrogen atmosphere at 0° C. and stirred for 1 h at 0° C. The mixture was quenched with 10 mL of water and filtered. The filtrate was concentrated under reduced pressure and the obtained aqueous solution was extracted with CHCl3. The organic layer was washed with brine and dried over MgSO4 and filtered. The filtrate was concentrated to afford titled compound as yellow oil (1.86 g, quant.).

Workup

  1. customThe mixture was quenched with 10 mL of water
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. extractionthe obtained aqueous solution was extracted with CHCl3
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5491b6cef9574ecb9c57726a2f821c14
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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