5-Chloro-1,3-dihydro-2-benzofuran-1-one → 5-Chloro-1,3-dihydroisobenzofuran-1-ol

HRID 2056744Notes

Reaction equation

HRID 2056744 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH:7]([OH:8])[O:6][CH2:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2417375-Chloro-1,3-dihydro-2-benzofuran-1-oneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 693101565-Chloro-1,3-dihydroisobenzofuran-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chlorophthalide (3.64 g, 21.6 mmol) in dichloromethane (100 mL) at −78° C. was added di-isobutylaluminium hydride (1M in toluene) (23.8 mL, 23.8 mmol) dropwise. After 1 h the reaction mixture was quenched with a saturated solution of sodium tartrate (250 mL), allowed to warm to room temperature and stirred for 1 h. The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to yield the title compound as a white solid.

Workup

  1. customAfter 1 h the reaction mixture was quenched with a saturated solution of sodium tartrate (250 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90efd2f51e8b47b0acab76f70b34e200
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

Loading…