Lithium tri-tert-butoxyaluminohydride → 1268842-81-4

HRID 2283428Notes

Reaction equation

HRID 2283428 reaction equation
[C:1]1([C:11](OCC)=[O:12])([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:3][CH2:2]1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[OH:12][CH2:11][C:1]1([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 8954485018721-65-8

Product 1

HCID 680062131268842-81-4

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 2 To a stirred solution of 1-tert-butyl 1-ethyl cyclopropane-1,1-dicarboxylate (0.5 g, 2.33 mmol) in THF (11.7 mL) at −78° C. was added lithium tri-tert-butoxyaluminum hydride solution (11.7 mL, 11.7 mmol) dropwise. The mixture was warmed to room temperature and stirred overnight before it was quenched at 0° C. by the addition of a saturated solution of potassium sodium tartrate. EtOAc was added the phases were separated and the aqueous phase was extracted into EtOAc (×2). Combined organic extracts were dried (Na2SO4), filtered and concentrated providing tert-butyl 1-(hydroxymethyl)-cyclopropane-1-carboxylate which was used without further purification, 0.438 g.

Workup

  1. customwas quenched at 0° C. by the addition of a saturated solution of potassium sodium tartrate
  2. additionEtOAc was added the phases
  3. customwere separated
  4. extractionthe aqueous phase was extracted into EtOAc (×2)
  5. dry with materialCombined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-75b34d99b7414989a1a25f56e77fc52c
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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