Diisobutylaluminum hydride → (R)-(4-azido-3,4-dihydro-2H-chromen-7-yl)methanol

HRID 2219876Notes

Reaction equation

HRID 2219876 reaction equation
[N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14](OC)=[O:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3].CC(C[AlH]CC(C)C)C>C1COCC1>[N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][OH:15])=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86604855(R)-methyl 4-azido-3,4-dihydro-2H-chromene-7-carboxylate

Product 1

HCID 59771815(R)-(4-azido-3,4-dihydro-2H-chromen-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-Methyl 4-azido-3,4-dihydro-2H-chromene-7-carboxylate (21.50 mmol, 1.0 eq) in 50 mL THF was cooled to 0° C., and treated with DIBAL (63.0 mmol, 3.0 eq). After 2.5 h, the reaction mixture was quenched by adding 50% saturated K—Na tartrate (60 mL). After stirring 1 h at room temperature, the solution was extracted with DCM (4×50 mL). The organic layers were then washed with water (2×50 mL), dried over MgSO4 and concentrated. The residue was purified using SiO2 chromatography (10→80% EtOAc/Hexanes) to afford the title compound.

Workup

  1. customthe reaction mixture was quenched
  2. additionby adding 50% saturated K—Na tartrate (60 mL)
  3. extractionthe solution was extracted with DCM (4×50 mL)
  4. washThe organic layers were then washed with water (2×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-d1486c22deea41b79c591f35c125ae71
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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