Diisobutylaluminum hydride → HCID 118324708, compound

HRID 587862Notes

Reaction equation

HRID 587862 reaction equation
[C:1]12([O:18][CH2:17][CH2:16][O:15]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][C@@H:3]([C:11](OC)=[O:12])[CH2:2]2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]12([O:15][CH2:16][CH2:17][O:18]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][C@@H:3]([CH:11]=[O:12])[CH2:2]2

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 90004235HCID 90004235, compound

Product 1

HCID 118324708HCID 118324708, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-methyl 3′,4′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-naphthalene]-3′-carboxylate (4.7 g, 18.93 mmol) in toluene (50 mL) and DCM (12.50 mL) to these solution of DIBAL-H (22.72 mL, 22.72 mmol) was added drop-wise at −78° C. under argon, and the mixture was stirred for 2 h at this temperature. Reaction mixture was quenched with aqueous NH4Cl solution at −78° C. and allowed to RT, filtered through celite, diluted with water (25 mL) and extracted with DCM (2×25 mL), dried over Na2SO4, filtered and concentrated to get the title compound (4.1 g) as an oil.

Workup

  1. customReaction mixture
  2. customwas quenched with aqueous NH4Cl solution at −78° C.
  3. customallowed to RT
  4. filtrationfiltered through celite
  5. additiondiluted with water (25 mL)
  6. extractionextracted with DCM (2×25 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9f9c296f30d54db58c7f40d518f9fa82
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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