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

HRID 645530

반응식

HRID 645530 반응식
[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.[CH3:14][OH:15]>O1CCCC1>[O:1]1[C:5]2[C:6]([CH2:14][OH:15])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 6331Borane2회HCID 27765552,3-Dihydro-1-benzofuran-2-carboxylic acid

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-933be0c6e7ba4f2b8a1f58234997e4e1
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704997B1

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