Methanol → (2,3-Dihydro-1-benzofuran-7-yl)methanol

HRID 1034981

Reaction equation

HRID 1034981 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1C(O)=O.B.B.[O:15]1CCC[CH2:16]1.CO>O1CCCC1>[O:1]1[C:5]2[C:6]([CH2:16][OH:15])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6331BoraneHCID 2723981Borane;tetrahydrofuranHCID 27765552,3-Dihydro-1-benzofuran-2-carboxylic acid

Product 1

HCID 2795020(2,3-Dihydro-1-benzofuran-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,3-Dihydrobenzofuran carboxylic acid (5.047 g) in tetrahydrofuran at −10° C. was treated dropwise with a solution of 1.0 M borane.tetrahydrofuran (20 mL). The temperature was allowed to warm to room temperature overnight, treated with additional 1.0 M borane-tetrahydrofuran (10 mL), and stirred at room temperature for 2 hours. The mixture was cooled to 5° C., slowly treated with methanol (20 mL), and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate (2×), saturated sodium chloride, dried (sodium sulfate), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:ethyl acetate, 3:2) to provide the title compound. MS (DCI/NH3) m/z 168 (M+NH4)+; 1H NMR (CDCl3) δ 3.21 (t, 2H), 4.60 (t, 2H), 4.68 (s, 2H), 6.83 (t, 1H), 7.08 (dd, 1H), 7.14 (dd, 1H).

Workup

  1. temperatureThe mixture was cooled to 5° C.
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate (2×), saturated sodium chloride
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (hexanes:ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-7b58b576bd784bd6939f0db169b83e10
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Linked notes

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