HCID 11850964, compound → HCID 59218416, compound

HRID 2246673Notes

Reaction equation

HRID 2246673 reaction equation
[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12](OCC)=[O:13])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([CH2:12][OH:13])[CH:3]=1

Participants

4

Reactant 2

HCID 11850964HCID 11850964, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 59218416HCID 59218416, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of the ester 46.4 (1.5 g, 6.9 mmol) in anhydrous THF (40 mL) is added dropwise a solution of LiAlH4 in THF (1.0 M, 13.7 mL, 13.7 mmol) at 0° C. The mixture is stirred until TLC confirms the consumption of the starting material. The reaction is slowly quenched with water (10 mL) at 0° C., 1N NaOH aqueous solution (50 mL) and another portion of water (10 mL). The mixture is filtered and the filtrate is extracted with EtOAc (3×100 mL), dried over MgSO4 and concentrated in vacuo. The residue is purified by column chromatography (silica, EtOAc/Hexane), to afford alcohol 46.5.

Workup

  1. customthe consumption of the starting material
  2. customThe reaction is slowly quenched with water (10 mL) at 0° C.
  3. filtrationThe mixture is filtered
  4. extractionthe filtrate is extracted with EtOAc (3×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica, EtOAc/Hexane)

Sources & evidence

ORD record
ord-ab4b9f045d5347b2afb373485f91c403
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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