Borane;tetrahydrofuran → (5-Chloro-4-methoxy-3-methyl benzofuran-2-yl)-methanol

HRID 29464Notes

Reaction equation

HRID 29464 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](O)=[O:11])=[C:7]([CH3:13])[C:6]=2[C:14]=1[O:15][CH3:16].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH3:13])[C:6]=2[C:14]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 687142675-Chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid

Product 1

HCID 68717159(5-Chloro-4-methoxy-3-methyl benzofuran-2-yl)-methanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.31 g (1.3 mmol) 5-chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid (Example 116, Step 3) in 10 mL of THF under nitrogen was added 1.0M BH3/THF solution (1.8 mL; 1.8 mmol; 1.4 eq). The reaction was stirred overnight and then quenched cautiously with water and extracted twice with ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and then brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give (5-chloro-4-methoxy-3-methyl benzofuran-2-yl)-methanol as a white crystalline solid (0.29 g; 99% yield).

Workup

  1. customquenched cautiously with water
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with 1N sodium hydroxide
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be140011399141829738b1a187fa21bf
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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