Aluminium lithium hydride → 2-(Naphtho[1,2-b]furan-3-yl)ethan-1-ol

HRID 1768023Notes

Reaction equation

HRID 1768023 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][C:12]1[C:13]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14]=2[O:15][CH:16]=1)C>C1COCC1>[O:15]1[CH:16]=[C:12]([CH2:11][CH2:10][OH:9])[C:13]2[CH:24]=[CH:23][C:22]3[C:17]([C:14]1=2)=[CH:18][CH:19]=[CH:20][CH:21]=3

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69455062Ethyl (naphtho[1,2-b]furan-3-yl)acetate

Product 1

HCID 236144482-(Naphtho[1,2-b]furan-3-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (200 mg, excess) in THF at 0° C., naphtho[1,2-b]furan-3-yl-acetic acid ethyl ester (1.27 g, 5 mmol) in THF (20 mL) was added slowly. After the addition, reaction mixture was stirred at room temperature for 1 hr and quenched with saturated NH4Cl solution. The product was extracted with chloroform and washed well with water. It was dried over anhydrous MgSO4; filtered and concentrated. The product, 2-naphtho[1,2-b]furan-3-yl ethanol, was obtained as white oil, was pure enough and taken to the next step without purification. Yield: 900 mg (84%); 213 (M+H).

Workup

  1. additionAfter the addition, reaction mixture
  2. customquenched with saturated NH4Cl solution
  3. extractionThe product was extracted with chloroform
  4. washwashed well with water
  5. dry with materialIt was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a8a7db9e1e584e988846aec3857f10df
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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