Diisobutylaluminum hydride → 3-Benzofuranol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,3-dihydro-

HRID 2118092Notes

Reaction equation

HRID 2118092 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]2[C:13](=[O:16])[CH2:14][O:15][C:11]=2[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>ClCCl>[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]2[CH:13]([OH:16])[CH2:14][O:15][C:11]=2[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 234389036-((Tert-butyldimethylsilyl)oxy)benzofuran-3(2H)-one

Product 1

HCID 590100533-Benzofuranol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,3-dihydro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 6-tert-Butyldimethylsilyloxy-2,3-dihydrobenzofuran-3-one (42 g, 158 mmol) in dichloromethane (1.4 L) at −78° C. under nitrogen was slowly added a solution of DIBAL-H (238 mL, 1.0 M, 238 mmol) in dichloromethane. The reaction was stirred at −78° C. for 1 h, and then was quenched carefully with ethyl acetate (1.0 L). Cold bath was removed, and a solution of Rochelle's salt (400 mL, 10%) was added continuously with stirring over a period of 2 h. The mixture was then diluted with MTBE (4.0 L), washed with brine, dried with magnesium sulfate, filtered and concentrated to yield the final product as yellow oil.

Workup

  1. customwas quenched carefully with ethyl acetate (1.0 L)
  2. customCold bath was removed
  3. additiona solution of Rochelle's salt (400 mL, 10%) was added continuously
  4. stirringwith stirring over a period of 2 h
  5. additionThe mixture was then diluted with MTBE (4.0 L)
  6. washwashed with brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9c1cc03ddab646e9be99dca75e498592
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

Loading…