HCID 58566366, compound → 5-chloro-7-(hydroxymethyl)-2,2-dimethylbenzofuran-3(2H)-one

HRID 1876394Notes

Reaction equation

HRID 1876394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14](O)=[O:15])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[C:6]=2[CH:13]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][OH:15])[C:5]2[O:9][C:8]([CH3:10])([CH3:11])[C:7](=[O:12])[C:6]=2[CH:13]=1

Participants

3

Reactant 1

HCID 58566366HCID 58566366, compound

Product 1

HCID 585665785-chloro-7-(hydroxymethyl)-2,2-dimethylbenzofuran-3(2H)-oneYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-chloro-2,2-dimethyl-3-oxo-2,3-dihydrobenzofuran-7-carboxylic acid (655) (2.67 g, 11.1 mmol) in tetrahydrofuran (56 mL) was added BH3.tetrahydrofuran (11.1 mL, 11.1 mmol) drop wise and stirred overnight. The reaction was quenched with water and methanol and then extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and then dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%) to afford 5-chloro-7-(hydroxymethyl)-2,2-dimethylbenzofuran-3(2H)-one (656) (278 mg). The saturated sodium bicarbonate layer was acidified to recover the starting acid (655) (1.68 g).

Workup

  1. customThe reaction was quenched with water and methanol
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%)

Sources & evidence

ORD record
ord-60a45c0a22734e34a3ea3650fb4d4087
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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