HCID 6105229, compound → HCID 13815773, compound

HRID 1506963Notes

Reaction equation

HRID 1506963 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH2:13]/[CH:14]=[CH:15]/[CH2:16][C:17](O)=[O:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:7]1([CH2:13]/[CH:14]=[CH:15]/[CH2:16][CH2:17][OH:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6105229HCID 6105229, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13815773HCID 13815773, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To stirred solution of LAH(LiAlH4, 3.3 g, 86.73 mmol) in THF(66 mL) was added dropwise a solution (E)-5-phenylpent-3-enoic acid (Preparation example 235, 11.0 g, 57.82 mmol) in THF(44 mL) at 0° C. then stirred at room temperature for 1 h. The reaction mixture was quenched with H2O at 0° C., filtered through celite, washed with EtOAc, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (7.2 g, 70˜90%)

Workup

  1. customThe reaction mixture was quenched with H2O at 0° C.
  2. filtrationfiltered through celite
  3. washwashed with EtOAc
  4. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-d6f16d7ec5e04a3ea1d8c540fab4b51d
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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