7-tert-Butyl-3,3-dimethyl-1-benzofuran-2(3H)-one → HCID 14672037, compound

HRID 352032Notes

Reaction equation

HRID 352032 reaction equation
[C:1]([C:5]1[C:13]2[O:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:16])([CH3:15])[CH2:11][OH:14])[C:13]=1[OH:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 146720367-tert-Butyl-3,3-dimethyl-1-benzofuran-2(3H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 14672037HCID 14672037, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 45 (235 mg, 1.077 mmol) in ether (5 ml) was dropwise added, with stirring and ice-cooling, to a suspension of LiAlH4 (49 mg, 1.29 mmol) in ether (5 ml). After washing a container of the solution with ether (5 ml), the washing was added to the mixture, which was warmed to room temperature and stirred for 45 minutes. The reaction mixture was added with ethyl acetate (1 ml) and 3 ml of a mixture of water and saturated ammonium chloride (1:1), and stirred for 30 minutes. Resultant slurry was removed by filtration through celite, and the filtrate was concentrated to obtain 253 mg (quant) of 46. 1H NMR (CDCl3) δ: 1.42 (9H, s, tBu), 1.44 (6H, s, 2×CH3), 3.81 (2H, s, CH2), 6.75-7.23 (3H, m, 3×Ar—H), 9.20 (1H, br s, phonemic-OH).

Workup

  1. washAfter washing a container of the solution with ether (5 ml)
  2. additionthe washing was added to the mixture, which
  3. stirringstirred for 45 minutes
  4. additionThe reaction mixture was added with ethyl acetate (1 ml) and 3 ml of a mixture of water and saturated ammonium chloride (1:1)
  5. stirringstirred for 30 minutes
  6. customResultant slurry was removed by filtration through celite
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f03c948dc5214b8b8b3a137576dfb989
Source dataset
uspto-grants-2004_06
Patent number
US06743923B2

Reaction notes

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