Methanol → (3,3-Dimethyl-2,3-dihydro-1-benzofuran-6-yl)methanol

HRID 878763Notes

Reaction equation

HRID 878763 reaction equation
[CH3:1][C:2]1([CH3:15])[C:6]2[CH:7]=[CH:8][C:9]([C:11](OC)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1.[BH4-].[Li+].CO.O>O1CCCC1>[CH3:1][C:2]1([CH3:15])[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 58279528Methyl 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylate

Product 1

HCID 68289793(3,3-Dimethyl-2,3-dihydro-1-benzofuran-6-yl)methanolYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3,3-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate (44 mg, 0.21 mmol) prepared in the method of US2009/105209 in tetrahydrofuran (1.5 mL) were added lithium borohydride (23 mg, 1.07 mmol) and methanol (43 μL, 1.07 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give the title compound (38 mg, 100%) as a colorless and clear oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c33acc6ee9a742cb834f8f60b2a8b7f1
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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