Sodium Hydroxide → (6-Fluorobenzofuran-3-YL)methanol

HRID 1929096Notes

Reaction equation

HRID 1929096 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[C:16]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=2[O:14][CH:13]=1)=O)C.[OH-].[Na+]>C1COCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([CH2:10][OH:9])=[CH:13][O:14][C:15]=2[CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66841592Ethyl 6-fluorobenzofuran-3-carboxylate

Product 1

HCID 66841405(6-Fluorobenzofuran-3-YL)methanolYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

1M LiAlH4-solution in THF (75.9 ml, 75.9 mmol) is diluted with 100 ml of THF and cooled to 0° C. 110 (7.9 g, 37.9 mmol) is dissolved in 100 ml of THF and added dropwise within 30 min. After completed addition the mixture is allowed to stir at rt for 2 h. Then the reaction mixture is cooled to −15° C. and 10 ml of a 1M NaOH solution is added very slowly. The mixture is filtrated over celite and evaporation under reduced pressure gave 5.3 g of a yellow oil.

Workup

  1. additionadded dropwise within 30 min
  2. additionaddition the mixture
  3. temperatureThen the reaction mixture is cooled to −15° C.
  4. filtrationThe mixture is filtrated over celite and evaporation under reduced pressure

Sources & evidence

ORD record
ord-6ad9eee235ed497f8bc83cb248d8620e
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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