Triphenylphosphine → 6-Allyl-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)3H-isobenzofuran-1-one

HRID 540714

반응식

HRID 540714 반응식
[CH2:1]([C:4]1[C:12]([OH:13])=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:14])=[C:6]([CH3:15])[C:5]=1[CH2:16][CH3:17])[CH:2]=[CH2:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:37][Si:38]([CH3:43])([CH3:42])[CH2:39][CH2:40]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:1]([C:4]1[C:12]([O:13][CH2:40][CH2:39][Si:38]([CH3:43])([CH3:42])[CH3:37])=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:14])=[C:6]([CH3:15])[C:5]=1[CH2:16][CH3:17])[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 180132-(Trimethylsilyl)ethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 574598626-allyl-5-ethyl-7-hydroxy-4-methyl-3H-isobenzofuran-1-one

생성물 1

HCID 574598636-Allyl-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)3H-isobenzofuran-1-one수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-allyl-5-ethyl-7-hydroxy-4-methyl-3H-isobenzofuran-1-one (199 mg, 0.857 mmol), PPh3 (337 mg, 1.286 mmol), and 2-trimethylsilylethanol in THF (3 mL) at 0° C. was added diisopropyl azodicarboxylate (259 mg, 1.286 mmol). The resulting yellow solution was allowed to warm to room temperature and stirred for one hour. The solvent was removed in vacuo and the crude material was dissolved in diethyl ether (3 mL). Hexanes (1.5 mL) were added. Triphenylphosphine oxide was removed by filtration and the filtrate was concentrated and purified by silica gel chromatography to provide the desired product (261 mg, 92%) as a clear oil. 1H NMR (300 MHz, CDCl3): δ=0.04 (s, 9H), 1.15 (t, J=7.8 Hz, 3H), 1.25 (m, 2H), 2.20 (s, 3H), 2.73 (q, J=7.8 Hz, 2H), 3.54 (m, 2H), 4.28 (m, 2H), 4.95 (d, J=17.1 Hz, 1H), 5.02 (d, J=10.2 Hz, 1H), 5.15 (s, 2H), 5.95 (m, 1H) ppm.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude material was dissolved in diethyl ether (3 mL)
  3. additionHexanes (1.5 mL) were added
  4. customTriphenylphosphine oxide was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-91a22acee0534dea84349cd094cb43e1
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871785B2

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