Triphenylphosphine → Chroman-7-ol

HRID 131158

반응식

HRID 131158 반응식
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:12].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[O:12]1[C:6]2[C:5](=[CH:10][CH:9]=[C:8]([OH:11])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 129584034-(3-Hydroxypropyl)benzene-1,3-diol

생성물 1

HCID 12236542Chroman-7-ol수율 66.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 4-(3-Hydroxy-propyl)-benzene-1,3-diol (3.05 g, 18.1 mmol, from Step 1) in anhydrous THF (50 mL ) were added Ph3P (7.13 g, 27.2 mmol, 1.5 eq) and ADDP (6.86 g, 27.2 mmol, 1.5 eq ) under argon. The mixture was stirred at rt for 17 h. The white solid was filtered off and the solvent was removed from the filtrate. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid (1.80 g, 60.5%). 1H-NMR (CD3CN) δ 6.87 (d, 1H), 6.70 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.2 Hz, 1H), 6.20 (d, 1H), 4.12 (t, 2H), 2.69 (t, 2H), 1.95 (m, 2H).

후처리

  1. filtrationThe white solid was filtered off
  2. customthe solvent was removed from the filtrate
  3. customThe residue was purified on silica gel (flash column chromatography)
  4. washeluting with 5% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-e754183c2b0548268128ce771017074e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384947B2

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