Dichloromethane → (4-Phenylfuran-3-yl)methanol

HRID 915671

반응식

HRID 915671 반응식
C([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][O:8][CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.C(Cl)Cl>C1(C)C=CC=CC=1>[C:11]1([C:10]2[C:6]([CH2:4][OH:3])=[CH:7][O:8][CH:9]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 15037153Ethyl-4-phenyl-3-furoateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 15037154(4-Phenylfuran-3-yl)methanol수율 72.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Prepare a solution of 4-phenylfuran-3-carboxylic acid ethyl ester (3.9 g, 18.1 mmol) in toluene (20 mL) under nitrogen at −78° C. Add a 1.0 M solution of Diisobutyl aluminium hydride in methylene chloride (35 mL, 35.0 mmol). Stir the reaction mixture for 1 hour, quench with water, and pour into 10% Rochelle's salt (200 mL). Extract the aqueous phase with ethyl acetate (2×200 mL). Wash the organic phase with brine (100 mL), dry (Na2SO4), filter, and concentrate. Flash chromatography on silica gel eluting with 4:1 Hex/ethyl acetate to afford 2.3 g of (4-phenylfuran-3-yl)methanol. 1H NMR (CDCl3) δ 7.51-7.58 (m, 4H), 7.30-7.45 (m, 3H), 4.67 (d, J=5 Hz, 2H).

후처리

  1. customquench with water
  2. additionpour into 10% Rochelle's salt (200 mL)
  3. extractionExtract the aqueous phase with ethyl acetate (2×200 mL)
  4. washWash the organic phase with brine (100 mL)
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate

출처 및 근거

ORD 기록
ord-6241da7920634465ac54be5c5f0f9452
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265246B2

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