Aluminium lithium hydride → HCID 90017866, compound

HRID 1506954Notes

Reaction equation

HRID 1506954 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C@@H:14]1[O:18][C:17]([CH3:20])([CH3:19])[O:16][C@H:15]1[C:21](OC)=[O:22]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C@@H:14]1[O:18][C:17]([CH3:19])([CH3:20])[O:16][C@H:15]1[CH2:21][OH:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118140878HCID 118140878, compound

Product 1

HCID 90017866HCID 90017866, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of To a solution LAH(LiAlH4 3.31 g, 87.25 mmol) in THF was added dropwise to a solution of (4R,5S)-methyl 5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (23.6 g, Preparation 26) in THF at 0° C., and the mixture stirred at room temp. The reaction mixture was quenched with H2O at 0° C., cellite filtered with EtOAc, 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 (21.13 g 70˜95%)

Workup

  1. customThe reaction mixture was quenched with H2O at 0° C.
  2. filtrationcellite filtered with EtOAc
  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-2b51a4ba6a7b45acb463f5bc8aa50bc9
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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